[1,2]-oxazine-3,5-diones

ABSTRACT

The present invention relates to novel [1,2]-oxazine-3,5-dione derivatives of the formula (I) 
     
       
         
         
             
             
         
       
         
         
           
             in which 
             W, X, Y, Z, G, D, A and B are as defined in the disclosure, to a plurality of processes for their preparation, and to their use as microbicides, pesticides and herbicides.

The present patent application has been filed under 35 U.S.C. 371 as anational stage application of PCT/EP02/13382, filed Nov. 27, 2002, whichwas published in German as International Patent Publication WO 03/048138on Jun. 12, 2003, which is entitled to the right of priority of GermanPatent Application 101 60 007.0, filed Dec. 6, 2001.

The present invention relates to novel [1,2]-oxazine-3,5-dionederivatives and their enols, to a plurality of processes for theirpreparation and to their use as microbicides, pesticides and herbicides.

4-Phenyl-substituted [1,2]-oxazine-3,5-diones were described asherbicides for the first time in WO 01/17972. Furthermore,4-acyl-substituted [1,2]-oxazine-3,5-diones were described as pesticidesand in particular as herbicides and growth regulators, for example inEP-A-39 48 89, WO 92/07837, U.S. Pat. No. 5,728,831.

This invention now provides novel compounds of the formula (I)

in which

-   W represents hydrogen, halogen, alkyl or alkoxy,-   X represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,-   Y in the 4-position represents hydrogen, alkoxy, halogen, cyano or    haloalkyl,-   Z in the 3- or 5-position represents hydrogen or alkyl,-   W also represents hydrogen, halogen or alkyl,-   X also represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or    cyano,-   Y in the 4-position also represents in each case optionally    substituted aryl or hetaryl,-   Z also represents hydrogen,-   W likewise represents hydrogen, halogen or alkyl,-   X likewise represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy    or cyano,-   Z likewise in the 5-position represents in each case optionally    substituted aryl or hetaryl,-   Y in the 4-position likewise represents hydrogen, alkyl or halogen,-   W moreover represents hydrogen, methyl, propyl, isopropyl or    halogen,-   X moreover represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy    or cyano,-   Z in the 3- or 5-position moreover represents hydrogen, halogen or    alkyl,-   Y in the 4-position moreover represents hydrogen, halogen, alkyl,    haloalkyl, cyano or haloalkoxy,-   A represents hydrogen, in each case optionally halogen-substituted    alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl,    saturated or unsaturated, optionally substituted cycloalkyl in which    optionally at least one ring atom is replaced by a heteroatom,-   B represents hydrogen, alkyl or alkoxyalkyl, or-   A and B together with the carbon atom to which they are attached    represent a saturated or unsaturated, unsubstituted or substituted    cycle which optionally contains at least one heteroatom,-   D represents hydrogen or an optionally substituted radical from the    group consisting of alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl,    alkylthioalkyl, saturated or unsaturated cycloalkyl in which    optionally one or more ring members are replaced by heteroatoms,-   G represents hydrogen (a) or represents a group

-    where    -   E represents a metal ion equivalent or an ammonium ion,    -   L represents oxygen or sulphur,    -   M represents oxygen or sulphur,    -   R¹ represents in each case optionally halogen-substituted alkyl,        alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or        optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl        which may be interrupted by at least one heteroatom, represents        in each case optionally substituted phenyl, phenylalkyl,        hetaryl, phenoxyalkyl or hetaryloxyalkyl,    -   R² represents in each case optionally halogen-substituted alkyl,        alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each case        optionally substituted cycloalkyl, phenyl or benzyl,    -   R³, R⁴ and R⁵ independently of one another represent in each        case optionally halogen-substituted alkyl, alkoxy, alkylamino,        dialkylamino, alkylthio, alkenylthio, cycloalkylthio or        represent in each case optionally substituted phenyl, benzyl,        phenoxy or phenylthio,    -   R⁶ and R⁷ independently of one another represent hydrogen, in        each case optionally halogen-substituted alkyl, cycloalkyl,        alkenyl, alkoxy, alkoxyalkyl, represent optionally substituted        phenyl, represent optionally substituted benzyl, or together        with the N atom to which they are attached represent a cycle        which is optionally interrupted by oxygen or sulphur.

Depending inter alia on the nature of the substituents, the compounds ofthe formula (I) can be present as geometrical and/or optical isomers orisomer mixtures of varying composition which, if desired, can beseparated in a customary manner. The present invention provides both thepure isomers and the isomer mixtures, their preparation and use, andalso compositions comprising them. However, hereinbelow, for the sake ofsimplicity, only compounds of the formula (I) are referred to, althoughthis is meant to be understood as including both the pure compounds and,if appropriate, mixtures with varying proportions of isomeric compounds.

Depending on the position of the substituent G, the compounds of theformula (I) can be present in the two isomeric forms of the formulae(I-A) and (I-B)

which is meant to be indicated by the broken line in formula (I).

The compounds of the formulae (I-A) and (I-B) can be present either asmixtures or in the form of their pure isomers. Mixtures of the compoundsof the formulae (I-A) and (I-B) can, if desired, be separated in amanner known per se by physical methods, for example by chromatographicmethods.

For the sake of improved clarity, hereinbelow only one of the possibleisomers is shown in each case. This does not exclude the fact that thecompounds may, if appropriate, be present in the form of the isomermixtures or in the other respective isomeric form.

Including the different meanings (a), (b), (c), (d), (e), (f) and (g) ofgroup G, the following principal structures (I-a) to (I-g) result

where

-   A, B, D, E, L, M, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are as    defined above.

Furthermore, it has been found that the novel compounds of the formula(I) are obtained by one of the processes described below:

-   (A) substituted phenyl-1,2-oxazine-3,5-diones and their enols of the    formula (I-a)

-    in which    -   A, B, D, W, X, Y and Z are as defined above,    -   are obtained when    -   N-acylhydroxyamino acid esters of the formula (II)

-   -   in which    -   A, B, D, W, X, Y and Z are as defined above    -   and    -   R⁸ represents alkyl (preferably C₁–C₆-alkyl)    -   are condensed intramolecularly in the presence of a diluent and        in the presence of a base.

Moreover, it has been found

-   (B) that compounds of the formula (I-b) shown above in which A, B,    D, R¹, W, X, Y and Z are as defined above are obtained when    compounds of the formula (I-a) shown above in which A, B, D, W, X, Y    and Z are as defined above are in each case reacted-   (α) with acid halides of the formula (III)

-    in which    -   R¹ is as defined above and    -   Hal represents halogen (in particular chlorine or bromine)    -   or-   (β) with carboxylic anhydrides of the formula (IV)    R¹—CO—O—CO—R¹  (IV)    -   in which    -   R¹ is as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;-   (C) that compounds of the formula (I-c) shown above in which A, B,    D, R², M, W, X, Y and Z are as defined above and L represents oxygen    are obtained when compounds of the formula (I-a) shown above in    which A, B, D, W, X, Y and Z are as defined above are in each case    reacted    -   with chloroformic esters or chloroformic thioesters of the        formula (V)        R²-M-CO—Cl  (V)    -   in which    -   R² and M are as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;-   (D) that compounds of the formula (I-c) shown above in which A, B,    D, R², M, W, X, Y and Z are as defined above and L represents    sulphur are obtained when compounds of the formula (I-a) shown above    in which A, B, D, W, X, Y and Z are as defined above are in each    case reacted    -   with chloromonothioformic esters or chlorodithioformic esters of        the formula (VI)

-   -   in which    -   M and R² are as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (E) that compounds of the formula (I-d) shown above in which A, B,    D, R³, W, X, Y and Z are as defined above are obtained when    compounds of the formula (I-a) shown above in which A, B, D, W, X, Y    and Z are as defined above are in each case reacted    -   with sulphonyl chlorides of the formula (VII)        R³—SO₂—Cl  (VII)    -   in which    -   R³ is as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (F) that compounds of the formula (I-e) shown above in which A, B,    D, L, R⁴, R⁵, W, X, Y and Z are as defined above are obtained when    compounds of the formula (I-a) shown above in which A, B, D, W, X, Y    and Z are as defined above are in each case reacted    -   with phosphorus compounds of the formula (VIII)

-   -   in which    -   L, R⁴ and R⁵ are as defined above and    -   Hal represents halogen (in particular chlorine or bromine),    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (G) that compounds of the formula (I-f) shown above in which A, B,    D, E, W, X, Y and Z are as defined above are obtained when compounds    of the formula (I-a) shown above in which A, B, D, W, X, Y and Z are    as defined above are in each case reacted    -   with metal compounds or amines of the formulae (IX) and (X),        respectively,

-   -   in which    -   Me represents a mono- or divalent metal (preferably an alkali        metal or alkaline earth metal, such as lithium, sodium,        potassium, magnesium or calcium),    -   t represents the number 1 or 2 and    -   R¹⁰, R¹¹, R¹² independently of one another represent hydrogen or        alkyl (preferably C₁–C₈-alkyl),    -   if appropriate in the presence of a diluent,

-   (H) that compounds of the formula (I-g) shown above in which A, B,    D, L, R⁶, R⁷, W, X, Y and Z are as defined above are obtained when    compounds of the formula (I-a) shown above in which A, B, D, W, X, Y    and Z are as defined above are in each case reacted

-   (α) with isocyanates or isothiocyanates of the formula (XI)    R⁶—N=C=L  (XI)    -   in which    -   R⁶ and L are as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of a catalyst, or

-   (β) with carbamoyl chlorides or thiocarbamoyl chlorides of the    formula (XII)

-    in which    -   L, R⁶ and R⁷ are as defined above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder.

Furthermore, it has been found that the novel compounds of the formula(I) have very good activity as pesticides, preferably as insecticides,acaricides and herbicides.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicalslisted in the formulae mentioned above and below are illustrated below:

-   W preferably represents hydrogen, halogen, C₁–C₆-alkyl or    C₁–C₆-alkoxy,-   X preferably represents halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy,    C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy or cyano,-   Y is preferably located in the 4-position and represents hydrogen,    C₁–C₆-alkoxy, halogen, cyano or C₁–C₄-haloalkyl,-   Z is preferably located in the 3- or 5-position and represents    hydrogen or C₁–C₆-alkyl,-   W also preferably represents hydrogen, halogen or C₁–C₆-alkyl,-   X also preferably represents halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy,    C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy or cyano,-   Y is also preferably located in the 4-position and represents the    radicals

-   Z also preferably represents hydrogen,-   V¹ also preferably represents hydrogen, halogen, C₁–C₁₂-alkyl,    C₁–C₆-alkoxy, C₁–C₆-alkylthio, C₁–C₆-alkylsulphinyl,    C₁–C₆-alkylsulphonyl, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, nitro,    cyano or represents phenyl, phenoxy, phenoxy-C₁–C₄-alkyl,    phenyl-C₁–C₄-alkoxy, phenylthio-C₁–C₄-alkyl or    phenyl-C₁–C₄-alkylthio, each of which is optionally mono- or    polysubstituted by halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy,    C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, nitro or cyano,-   V² and V³ independently of one another also preferably represent    hydrogen, halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₄-haloalkyl or    C₁–C₄-haloalkoxy,-   V¹ and V² together also preferably represent C₃–C₄-alkanediyl which    may optionally be substituted by halogen and/or C₁–C₂-alkyl and    which may optionally be interrupted by one or two oxygen atoms,-   W likewise preferably represents hydrogen, halogen or C₁–C₆-alkyl,-   X likewise preferably represents halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy,    C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy or cyano,-   Z likewise preferably in the 5-position represents the radicals

-   Y likewise preferably in the 4-position represents hydrogen,    C₁–C₆-alkyl or halogen,-   V¹ likewise preferably represents hydrogen, halogen, C₁–C₁₂-alkyl,    C₁–C₆-alkoxy, C₁–C₆-alkylthio, C₁–C₆-alkylsulphinyl,    C₁–C₆-alkylsulphonyl, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, nitro,    cyano or represents phenyl, phenoxy, phenoxy-C₁–C₄-alkyl,    phenyl-C₁–C₄-alkoxy, phenylthio-C₁–C₄-alkyl or    phenyl-C₁–C₄-alkylthio, each of which is optionally mono- or    polysubstituted by halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy,    C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, nitro or cyano,-   V² and V³ likewise preferably independently of one another represent    hydrogen, halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₄-haloalkyl or    C₁–C₄-haloalkoxy,-   V¹ and V² together likewise preferably represent C₃–C₄-alkanediyl    which may optionally be substituted by halogen and/or C₁–C₂-alkyl    and which may optionally be interrupted by one or two oxygen atoms,-   W moreover preferably represents hydrogen, methyl, propyl, isopropyl    or halogen,-   X moreover preferably represents halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy,    C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy or cyano,-   Z moreover preferably in the 3- or 5-position represents hydrogen,    halogen or C₁–C₆-alkyl,-   Y moreover preferably in the 4-position represents hydrogen,    halogen, C₁–C₆-alkyl, C₁–C₄-haloalkyl, cyano or C₁–C₄-haloalkoxy,-   A preferably represents hydrogen or in each case optionally    halogen-substituted C₁–C₁₂-alkyl, C₃–C₈-alkenyl,    C₁–C₁₀-alkoxy-C₁–C₈-alkyl, poly-C₁–C₈-alkoxy-C₁–C₈-alkyl,    C₁–C₁₀-alkylthio-C₁–C₆-alkyl, optionally halogen-, C₁–C₆-alkyl- or    C₁–C₆-alkoxy-substituted C₃–C₈-cycloalkyl in which optionally one or    two not directly adjacent ring members are replaced by oxygen and/or    sulphur,-   B preferably represents hydrogen, C₁–C₁₂-alkyl or    C₁–C₈-alkoxy-C₁–C₆-alkyl or-   A, B and the carbon atom to which they are attached preferably    represent saturated C₃–C₁₀-cycloalkyl or unsaturated    C₅–C₁₀-cycloalkyl in which optionally one ring member is replaced by    oxygen or sulphur and which are optionally mono- or disubstituted by    C₁–C₈-alkyl, C₃–C₁₀-cycloalkyl, C₁–C₈-haloalkyl, C₁–C₈-alkoxy,    C₁–C₈-alkylthio, halogen or phenyl,-   D preferably represents hydrogen, in each case optionally    halogen-substituted C₁–C₁₂-alkyl, C₃–C₈-alkenyl,    C₁–C₁₀-alkoxy-C₂–C₈-alkyl, poly-C₁–C₈-alkoxy-C₂–C₈-alkyl,    C₁–C₁₀-alkylthio-C₂–C₈-alkyl, optionally halogen-, C₁–C₄-alkyl-,    C₁–C₄-alkoxy- or C₁–C₄-haloalkyl-substituted C₃–C₈-cycloalkyl in    which optionally one ring member is replaced by oxygen or sulphur,-   G preferably represents hydrogen (a) or represents one of the groups

in particular (a), (b) or (c),

-   -   in which    -   E represents a metal ion equivalent or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,

-   R¹ preferably represents in each case optionally halogen-substituted    C₁–C₂₀-alkyl, C₂–C₂₀-alkenyl, C₁–C₈-alkoxy-C₁–C₈-alkyl,    C₁–C₈-alkylthio-C₁–C₈-alkyl, poly-C₁–C₈-alkoxy-C₁–C₈-alkyl or    optionally halogen-, C₁–C₆-alkyl- or C₁–C₆-alkoxy-substituted    C₃–C₈-cycloalkyl in which optionally one or more (preferably not    more than two) not directly adjacent ring members are replaced by    oxygen and/or sulphur,    -   represents optionally halogen-, cyano-, nitro-, C₁–C₆-alkyl-,        C₁–C₆-alkoxy-, C₁–C₆-haloalkyl-, C₁–C₆-haloalkoxy-,        C₁–C₆-alkylthio- or C₁–C₆-alkyl-sulphonyl-substituted phenyl,    -   represents optionally halogen-, nitro-, cyano-, C₁–C₆-alkyl-,        C₁–C₆-alkoxy-, C₁–C₆-haloalkyl- or C₁–C₆-haloalkoxy-substituted        phenyl-C₁–C₆-alkyl,    -   represents optionally halogen- or C₁–C₆-alkyl-substituted 5- or        6-membered hetaryl (for example pyrazolyl, thiazolyl, pyridyl,        pyrimidyl, furanyl or thienyl),    -   represents optionally halogen- or C₁–C₆-alkyl-substituted        phenoxy-C₁–C₆-alkyl or    -   represents optionally halogen-, amino- or        C₁–C₆-alkyl-substituted 5- or 6-membered hetaryloxy-C₁–C₆-alkyl        (for example pyridyloxy-C₁–C₆-alkyl, pyrimidyloxy-C₁–C₆-alkyl or        thiazolyloxy-C₁–C₆-alkyl),

-   R² preferably represents in each case optionally halogen-substituted    C₁–C₂₀-alkyl, C₂–C₂₀-alkenyl, C₁–C₈-alkoxy-C₂–C₈-alkyl,    poly-C₁–C₈-alkoxy-C₂–C₈-alkyl,    -   represents optionally halogen-, C₁–C₆-alkyl- or        C₁–C₆-alkoxy-substituted C₃–C₈-cycloalkyl or    -   represents in each case optionally halogen-, cyano-, nitro-,        C₁–C₆-alkyl-, C₁–C₆-alkoxy-, C₁–C₆-haloalkyl- or        C₁–C₆-haloalkoxy-substituted phenyl or benzyl,

-   R³ preferably represents optionally halogen-substituted C₁–C₈-alkyl    or represents in each case optionally halogen-, C₁–C₆-alkyl-,    C₁–C₆-alkoxy-, C₁–C₄-haloalkyl-, C₁–C₄-haloalkoxy-, cyano- or    nitro-substituted phenyl or benzyl,

-   R⁴ and R⁵ independently of one another preferably represent in each    case optionally halogen-substituted C₁–C₈-alkyl, C₁–C₈-alkoxy,    C₁–C₈-alkylamino, di-(C₁–C₈-alkyl)amino, C₁–C₈-alkylthio,    C₂–C₈-alkenylthio, C₃–C₇-cycloalkylthio or represent in each case    optionally halogen-, nitro-, cyano-, C₁–C₄-alkoxy-,    C₁–C₄-haloalkoxy-, C₁–C₄-alkylthio-, C₁–C₄-haloalkylthio-,    C₁–C₄-alkyl- or C₁–C₄-haloalkyl-substituted phenyl, phenoxy or    phenylthio,

-   R⁶ and R⁷ independently of one another preferably represent    hydrogen, represent in each case optionally halogen-substituted    C₁–C₈-alkyl, C₃–C₈-cycloalkyl, C₁–C₈-alkoxy, C₃–C₈-alkenyl,    C₁–C₈-alkoxy-C₁–C₈-alkyl, represent optionally halogen-,    C₁–C₈-haloalkyl-, C₁–C₈-alkyl- or C₁–C₈-alkoxy-substituted phenyl,    optionally halogen-, C₁–C₈-alkyl-, C₁–C₈-haloalkyl- or    C₁–C₈-alkoxy-substituted benzyl or together with the nitrogen atom    to which they are attached represent optionally    C₁–C₄-alkyl-substituted C₄–C₇-cycloalkyl in which optionally one    carbon atom is replaced by oxygen or sulphur.

In the radical definitions mentioned as being preferred, halogenrepresents fluorine, chlorine, bromine and iodine, in particularfluorine, chlorine and bromine.

-   W particularly preferably represents hydrogen, chlorine, bromine,    C₁–C₄-alkyl or C₁–C₄-alkoxy,-   X particularly preferably represents chlorine, bromine, C₁–C₄-alkyl,    C₁–C₄-alkoxy, C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy or cyano,-   Y particularly preferably in the 4-position represents hydrogen,    C₁–C₄-alkoxy, chlorine, bromine, cyano or C₁–C₂-haloalkoxy,-   Z particularly preferably in the 3- or 5-position represents    hydrogen or C₁–C₄-alkyl,-   W also particularly preferably represents hydrogen, chlorine,    bromine or C₁–C₄-alkyl,-   X also particularly preferably represents chlorine, bromine,    C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy or    cyano,-   Y also particularly preferably in the 4-position represents the    radicals

-   Z particularly preferably represents hydrogen,-   V¹ also particularly preferably represents hydrogen, fluorine,    chlorine, bromine, C₁–C₆-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl,    C₁–C₂-haloalkoxy, nitro, cyano or phenyl which is in each case    optionally mono- or disubstituted by fluorine, chlorine, bromine,    C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy, nitro    or cyano,-   V² and V³ independently of one another also particularly preferably    represent hydrogen, fluorine, chlorine, bromine, C₁–C₄-alkyl,    C₁–C₄-alkoxy, C₁–C₂-haloalkyl or C₁–C₂-haloalkoxy,-   V¹ and V² together also particularly preferably represent —O—CH₂—O—    or —O—CF₂—O—,-   W likewise particularly preferably represents hydrogen, chlorine,    bromine or C₁–C₄-alkyl,-   X likewise particularly preferably represents chlorine, C₁–C₄-alkyl    or C₁–C₂-haloalkyl,-   Z likewise particularly preferably in the 5-position represents the    radicals

-   Y likewise particularly preferably in the 4-position represents    hydrogen, C₁–C₄-alkyl or chlorine,-   V¹ likewise particularly preferably represents hydrogen, fluorine,    chlorine, bromine, C₁–C₆-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl,    C₁–C₂-haloalkoxy, nitro, cyano or represents phenyl which is    optionally mono- or disubstituted by fluorine, chlorine, bromine,    C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy, nitro    or cyano,-   V² and V³ likewise independently of one another particularly    preferably represent hydrogen, fluorine, chlorine, bromine,    C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl or C₁–C₂-haloalkoxy,-   V¹ and V² together likewise particularly preferably represent    —O—CH₂—O— or —O—CF₂—O—,-   W moreover particularly preferably represents hydrogen, methyl,    chlorine or bromine,-   X moreover particularly preferably represents chlorine, bromine,    C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy or    cyano,-   Z moreover particularly preferably in the 3- or 5-position    represents hydrogen, chlorine, bromine or C₁–C₄-alkyl,-   Y moreover particularly preferably in the 4-position represents    hydrogen, chlorine, bromine, C₁–C₄-alkyl, C₁–C₂-haloalkyl, cyano or    C₁–C₂-haloalkoxy,-   A particularly preferably represents hydrogen, represents    C₁–C₁₀-alkyl, C₁–C₈-alkoxy-C₁–C₆-alkyl, each of which is optionally    mono- to trisubstituted by fluorine or chlorine, represents    C₃–C₇-cycloalkyl which is optionally mono- or disubstituted by    fluorine, chlorine, C₁–C₄-alkyl or C₁–C₄-alkoxy and in which    optionally one ring member is replaced by oxygen or sulphur,-   B particularly preferably represents hydrogen or C₁–C₆-alkyl or-   A, B and the carbon atom to which they are attached particularly    preferably represent saturated or unsaturated C₅–C₇-cycloalkyl in    which optionally one ring member is replaced by oxygen or sulphur    and which is optionally monosubstituted by C₁–C₆-alkyl,    C₅–C₈-cycloalkyl, C₁–C₃-haloalkyl or C₁–C₆-alkoxy or-   D particularly preferably represents hydrogen, represents    C₁–C₁₀-alkyl, C₃–C₆-alkenyl, C₁–C₆-alkoxy-C₂–C₄-alkyl or    C₁–C₄-alkylthio-C₂–C₄-alkyl, each of which is optionally mono- to    trisubstituted by fluorine or chlorine, represents optionally    fluorine-, chlorine-, C₁–C₄-alkyl-, C₁–C₄-alkoxy- or    C₁–C₂-haloalkyl-substituted C₃–C₇-cycloalkyl in which optionally one    methylene group is replaced by oxygen or sulphur,-   G particularly preferably represents hydrogen (a) or represents one    of the groups

in particular (a), (b) or (c),

-   -   in which    -   E represents a metal ion equivalent or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,

-   R¹ particularly preferably represents C₁–C₁₆-alkyl, C₂–C₁₆-alkenyl,    C₁–C₆-alkoxy-C₁–C₆-alkyl, C₁–C₄-alkylthio-C₁–C₄-alkyl,    poly-C₁–C₄-alkoxy-C₁–C₄-alkyl, each of which is optionally mono- to    trisubstituted by fluorine or chlorine, or represents    C₃–C₇-cycloalkyl which is optionally mono- or disubstituted by    fluorine, chlorine, C₁–C₄-alkyl or C₁–C₄-alkoxy and in which    optionally one or two not directly adjacent ring members are    replaced by oxygen and/or sulphur,    -   represents phenyl which is optionally mono- or disubstituted by        fluorine, chlorine, bromine, cyano, nitro, C₁–C₄-alkyl,        C₁–C₄-alkoxy, C₁–C₃-haloalkyl, C₁–C₃-haloalkoxy, C₁–C₄-alkylthio        or C₁–C₄-alkylsulphonyl,    -   represents phenyl-C₁–C₄-alkyl which is optionally mono- or        disubstituted by fluorine, chlorine, bromine, C₁–C₄-alkyl,        C₁–C₄-alkoxy, C₁–C₃-haloalkyl or C₁–C₃-haloalkoxy,    -   represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or        thienyl, each of which is optionally monosubstituted by        fluorine, chlorine, bromine or C₁–C₄-alkyl,    -   represents phenoxy-C₁–C₃-alkyl which is optionally mono- or        disubstituted by fluorine, chlorine, bromine or C₁–C₄-alkyl,

-   R² particularly preferably represents C₁–C₁₆-alkyl, C₂–C₁₆-alkenyl,    C₁–C₆-alkoxy-C₂–C₆-alkyl or poly-C₁–C₆-alkoxy-C₂–C₆-alkyl, each of    which is optionally mono- to trisubstituted by fluorine,    -   represents C₃–C₇-cycloalkyl which is optionally mono- or        disubstituted by fluorine, chlorine, C₁–C₄-alkyl or C₁–C₄-alkoxy        or    -   represents phenyl or benzyl, each of which is optionally mono-        or disubstituted by fluorine, chlorine, bromine, cyano, nitro,        C₁–C₄-alkyl, C₁–C₃-alkoxy, C₁–C₃-haloalkyl or C₁–C₃-haloalkoxy,

-   R³ particularly preferably represents C₁–C₆-alkyl which is    optionally mono- to trisubstituted by fluorine or represents phenyl    or benzyl, each of which is optionally mono- or disubstituted by    fluorine, chlorine, bromine, C₁–C₄-alkyl, C₁–C₄-alkoxy,    C₁–C₃-haloalkyl, C₁–C₃-haloalkoxy, cyano or nitro,

-   R⁴ particularly preferably represents C₁–C₆-alkyl, C₁–C₆-alkoxy,    C₁–C₆-alkylamino, di-(C₁–C₆-alkyl)amino, C₁–C₆-alkylthio,    C₃–C₄-alkenylthio, C₃–C₆-cycloalkylthio or represents phenyl,    phenoxy or phenylthio, each of which is optionally mono- or    disubstituted by fluorine, chlorine, bromine, nitro, cyano,    C₁–C₃-alkoxy, C₁–C₃-haloalkoxy, C₁–C₃-alkylthio,    C₁–C₃-haloalkylthio, C₁–C₃-alkyl or C₁–C₃-haloalkyl,

-   R⁵ particularly preferably represents C₁–C₄-alkoxy or    C₁–C₄-alkylthio,

-   R⁶ particularly preferably represents C₁–C₆-alkyl, C₃–C₆-cycloalkyl,    C₁–C₆-alkoxy, C₃–C₆-alkenyl, C₁–C₆-alkoxy-C₁–C₆-alkyl, represents    phenyl which is optionally mono- or disubstituted by fluorine,    chlorine, bromine, C₁–C₃-haloalkyl, C₁–C₄-alkyl or C₁–C₄-alkoxy,    represents benzyl which is optionally mono- or disubstituted by    fluorine, chlorine, bromine, C₁–C₄-alkyl, C₁–C₃-haloalkyl or    C₁–C₄-alkoxy,

-   R⁷ particularly preferably represents hydrogen, C₁–C₆-alkyl or    C₃–C₆-alkenyl,

-   R⁶ and R⁷ together with the nitrogen atom to which they are attached    particularly preferably represent C₅–C₆-cycloalkyl which is    optionally mono- or disubstituted by methyl or ethyl and in which    optionally one methylene group is replaced by oxygen or sulphur.    -   In the radical definitions mentioned as being particularly        preferred, halogen represents fluorine, chlorine and bromine, in        particular fluorine and chlorine.

-   W very particularly preferably represents hydrogen, chlorine,    methyl, ethyl or methoxy,

-   X very particularly preferably represents chlorine, bromine, methyl,    ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy,    trifluoroethoxy or cyano,

-   Y very particularly preferably in the 4-position represents    hydrogen, methoxy, chlorine, bromine or trifluoromethyl,

-   Z very particularly preferably in the 3- or 5-position represents    hydrogen or methyl,

-   W also very particularly preferably represents hydrogen, chlorine,    bromine or methyl,

-   X also very particularly preferably represents chlorine, bromine,    methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy or    cyano,

-   Y also very particularly preferably in the 4-position represents the    radical

-   Z also very particularly preferably represents hydrogen,-   V¹ also very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, tert-butyl,    methoxy, ethoxy, n-propoxy, isopropoxy, trifluoromethyl or    trifluoromethoxy,-   V² also very particularly preferably represents hydrogen, fluorine,    chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy or    trifluoromethyl,-   W likewise very particularly preferably represents hydrogen,    chlorine or methyl,-   X likewise very particularly preferably represents chlorine, methyl    or trifluoromethyl,-   Z likewise very particularly preferably in the 5-position represents    the radical

-   Y likewise very particularly preferably in the 4-position represents    hydrogen or methyl,-   V¹ likewise very particularly preferably represents hydrogen,    fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl,    tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, trifluoromethyl    or trifluoromethoxy,-   V² likewise very particularly preferably represents hydrogen,    fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy,    ethoxy or trifluoromethyl,-   W moreover very particularly preferably represents hydrogen, methyl,    chlorine or bromine,-   X moreover very particularly preferably represents chlorine,    bromine, methyl, methoxy, trifluoromethyl, difluoromethoxy,    trifluoroethoxy or cyano,-   Z moreover very particularly preferably in the 3- or 5-position    represents hydrogen, chlorine, bromine or methyl,-   Y moreover very particularly preferably in the 4-position represents    hydrogen, chlorine, bromine, methyl, trifluoromethyl or    trifluoromethoxy,-   A very particularly preferably represents hydrogen, C₁–C₄-alkyl or    C₁–C₄-alkoxy-C₁–C₂-alkyl, or represents C₃–C₆-cycloalkyl which is    optionally monosubstituted by fluorine, methyl, ethyl or methoxy and    in which optionally one ring member is replaced by oxygen or    sulphur,-   B very particularly preferably represents hydrogen, methyl or ethyl    or-   A, B and the carbon atom to which they are attached very    particularly preferably represent saturated C₅–C₆-cycloalkyl, in    which optionally one ring member is replaced by oxygen and which is    optionally monosubstituted by methyl, ethyl, propyl, isopropyl,    butyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy or    isobutoxy,-   D very particularly preferably represents hydrogen, represents    C₁–C₈-alkyl, C₃–C₄-alkenyl, C₁–C₆-alkoxy-C₂–C₄-alkyl,    C₁–C₄-alkylthio-C₂–C₄-alkyl or C₃–C₆-cycloalkyl, each of which is    optionally mono- to trisubstituted by fluorine,-   G very particularly preferably represents hydrogen (a) or represents    one of the groups

in particular (a), (b) or (c),

-   -   in which    -   E represents a metal ion equivalent or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,

-   R¹ very particularly preferably represents C₁–C₁₀-alkyl,    C₂–C₁₀-alkenyl, C₁–C₂-alkoxy-C₁–C₂-alkyl,    C₁–C₂-alkylthio-C₁–C₂-alkyl, each of which is optionally mono- to    trisubstituted by fluorine or chlorine, or represents    C₃–C₆-cycloalkyl which is optionally mono- or disubstituted by    fluorine, chlorine, methyl, ethyl, propyl, i-propyl, butyl, i-butyl,    tert-butyl, methoxy, ethoxy, n-propoxy or isopropoxy and in which    optionally one ring member is replaced by oxygen,    -   represents phenyl which is optionally mono- or disubstituted by        fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl,        n-propyl, i-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl        or trifluoromethoxy,    -   represents benzyl which is optionally mono- or disubstituted by        fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or        trifluoromethoxy,    -   represents furanyl, thienyl, pyridyl, pyrimidyl, thiazolyl or        pyrazolyl, each of which is optionally substituted by fluorine,        chlorine, bromine, methyl or ethyl,

-   R² very particularly preferably represents C₁–C₁₀-alkyl,    C₂–C₁₀-alkenyl or C₁–C₄-alkoxy-C₂–C₃-alkyl, each of which is    optionally mono- to trisubstituted by fluorine,    -   represents C₃–C₆-cycloalkyl which is optionally monosubstituted        by fluorine, chlorine, methyl, ethyl or methoxy,    -   or represents phenyl or benzyl, each of which is optionally        monosubstituted by fluorine, chlorine, cyano, nitro, methyl,        ethyl, n-propyl, i-propyl, methoxy, ethoxy, trifluoromethyl or        trifluoromethoxy,

-   R³ very particularly preferably represents methyl, ethyl, n-propyl    or represents phenyl which is optionally monosubstsituted by    fluorine, chlorine, bromine, methyl, tert-butyl, methoxy,    trifluoromethyl, trifluoromethoxy, cyano or nitro,

-   R⁴ very particularly preferably represents C₁–C₄-alkyl,    C₁–C₄-alkoxy, C₁–C₄-alkylamino, di-(C₁–C₄-alkyl)amino,    C₁–C₄-alkylthio or represents phenoxy or phenylthio, each of which    is optionally monosubstituted by fluorine, chlorine, bromine, nitro,    cyano, C₁–C₂-alkoxy, C₁–C₂-fluoroalkoxy, C₁–C₂-alkylthio,    C₁–C₂-fluoroalkylthio or C₁–C₃-alkyl,

-   R⁵ very particularly preferably represents methoxy, ethoxy,    methylthio or ethylthio,

-   R⁶ very particularly preferably represents C₁–C₄-alkyl,    C₃–C₆-cycloalkyl, C₁–C₄-alkoxy, C₃–C₄-alkenyl,    C₁–C₄-alkoxy-C₁–C₄-alkyl, represents phenyl which is optionally    mono- or disubstituted by fluorine, chlorine, bromine,    trifluoromethyl, methyl or methoxy, represents benzyl which is    optionally monosubstituted by fluorine, chlorine, bromine, methyl,    trifluoromethyl or methoxy,

-   R⁷ very particularly preferably represents hydrogen, methyl, ethyl,    propyl, isopropyl, butyl or allyl,    -   or

-   R⁶ and R⁷ together with the nitrogen atom to which they are attached    very particularly preferably represent C₅–C₆-cycloalkyl which is    optionally mono- or disubstituted by methyl and in which optionally    one methylene group is replaced by oxygen.

-   W especially preferably represents hydrogen, methyl, ethyl or    chlorine,

-   X especially preferably represents methyl or chlorine,

-   Y especially preferably in the 4-position represents methoxy,    chlorine, bromine or trifluoromethyl,

-   Z especially preferably in the 5-position represents hydrogen or    methyl,

-   A especially preferably represents methyl,

-   B especially preferably represents methyl,

-   D especially preferably represents methyl or hydrogen, very    especially preferably methyl,

-   G especially preferably represents hydrogen,

-   W likewise especially preferably represents hydrogen,

-   X likewise especially preferably represents methyl or chlorine,

-   Z likewise especially preferably in the 5-position represents

-   Y likewise especially preferably represents hydrogen,-   A likewise especially preferably represents methyl,-   B likewise especially preferably represents methyl,-   A and B together likewise especially preferably represent —(CH₂)₃—,-   D likewise especially preferably represents methyl,-   G likewise especially preferably represents hydrogen (a) or    represents one of the groups

-   R¹ likewise especially preferably represents C₁–C₆-alkyl,-   R² likewise especially preferably represents C₁–C₆-alkyl,-   W moreover especially preferably represents hydrogen or methyl,-   X moreover especially preferably represents methyl or bromine,-   Z moreover especially preferably in the 3- or 5-position represents    hydrogen or methyl,-   Y moreover especially preferably in the 4-position represents    methyl,-   A moreover especially preferably represents methyl,-   B moreover especially preferably represents methyl,-   A and B together moreover especially preferably represent —(CH₂)₄—,-   D moreover especially preferably represents methyl,-   G moreover especially preferably represents hydrogen (a) or    represents one of the groups

-   R¹ moreover especially preferably represents C₁–C₆-alkyl,-   R² moreover especially preferably represents C₁–C₆-alkyl.

The general or preferred radical definitions or illustrations listedabove can be combined with one another as desired, i.e. includingcombinations between the respective ranges and preferred ranges. Thedefinitions apply both to the end products and, correspondingly, toprecursors and intermediates.

Preference according to the invention is given to compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Especially preferred according to the invention are the compounds of theformula (I) which contain a combination of the meanings listed above asbeing especially preferred.

Especially preferred are compounds of the formula (I) where Z representsoptionally substituted aryl.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched as far as this ispossible, including in combination with heteroatoms, such as, forexample, in alkoxy.

Unless defined otherwise, optionally substituted radicals can be mono-or polysubstituted, where in the case of polysubstitutions thesubstituents can be identical or different.

Using, for example, according to process (A), ethylN-methyl-N-[(6-methyl-3-phenyl)phenylacetyl]-1-aminooxycyclopentanecarboxylateas starting material, the course of the process according to theinvention can be represented by the reaction scheme below:

Using, for example, according to process (Bα),2-methyl-4-[(2-chloro-5-(3-chlorophenyl))phenyl]-6,6-dimethyl-[1,2]-oxazine-3,5-dioneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the reaction schemebelow:

Using, for example, according to process (B) (variant β),2-ethyl-4-(2,5-dimethylphenyl)-6,6-dimethyl-[1,2]-oxazine-3,5-dione andacetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the reaction schemebelow:

Using, for example, according to process (C),2-methyl-4-(2,4,6-trimethylphenyl)-6,6-dimethyl-[1,2]-oxazine-3,5-dioneand ethoxyethyl chloroformate as starting materials, the course of theprocess according to the invention can be represented by the reactionscheme below:

Using, for example, according to process (D),2-methyl-4-(2,5-dichlorophenyl)-6,6-dimethyl-[1,2]-oxazine-3,5-dione andmethyl chloromonothioformate as starting materials, the course of thereaction can be represented as follows:

Using, for example, according to process (E),2-methyl-4-(2,4,6-trimethylphenyl)-6,6-pentamethylene-[1,2]-oxazine-3,5-dioneand methanesuphonyl chloride as starting materials, the course of thereaction can be represented by the reaction scheme below:

Using, for example, according to process (F),2-methyl-4-(4-chloro-2,6-dimethylphenyl)-6,6-dimethyl-[1,2]-oxazine-3,5-dioneand 2,2,2-trifluoroethyl methanethiophosphonyl chloride as startingmaterials, the course of the reaction can be represented by the reactionscheme below:

Using, for example, according to process (G),2-methyl-4-[2-methyl-5-(4-chlorophenyl)phenyl]-6,6-dimethyl-[1,2]-oxazine-3,5-dioneand NaOH as components, the course of the process according to theinvention can be represented by the reaction scheme below:

Using, for example, according to process (H) (variant α),2-methyl-5-(2,4-dimethylphenyl)-6,6-pentamethylene-[1,2]-oxazine-3,5-dioneand ethyl isocyanate as starting materials, the course of the reactioncan be represented by the reaction scheme below:

Using, for example, according to process (H) (variant β),2-methyl-4-[2-chloro-5-(4-chlorophenyl)phenyl]-6,6-dimethyl-[1,2]-oxazine-3,5-dioneand dimethylcarbamoyl chloride as starting materials, the course of thereaction can be represented by the scheme below:

The compounds, required as starting materials in the process (a)according to the invention, of the formula (II)

in which

-   A, B, D, W, X, Y, Z and R⁸ are as defined above,-   are novel.

The acylhydroxylamino acid esters of the formula (II) are obtained, forexample, when amino acid derivatives of the formula (XIII)

in which

-   A, B, R⁸ and D are as defined above,    are acylated with substituted phenylacetyl halides of the formula    (XIV)

in which

-   W, X, Y and Z are as defined above und-   Hal represents chlorine or bromine

(Chem. Reviews 52, 237–416 (1953); Bhattacharya, Indian J. Chem. 6,341–5, 1968).

Some of the hydroxylamino acid esters, required as starting materialsfor preparing compounds of the formula (II), of the formula (XIII)

in which

-   A, B and R⁸ are as defined above are novel, and they can be prepared    by known processes (N. A. Porter et al. J. Org. Chem. 63 5547    (1998)).

Thus, hydroxylamino acid esters of the formula (XIII)

in which

-   A, B and R⁸ are as defined above are obtained, for example, when    N-hydroxyphthalimide of the formula (XV)

is reacted with haloalkyl esters of the formula (XVI)

in which

-   A, B and R⁸ are as defined above-   and-   Hal represents chlorine, bromine or iodine, preferably bromine, to    give O-alkoxyphthalimides of the formula (XVII),

in which

-   A, B and R⁸ are as defined above-   and the compounds of the formula (XIII-a) are released from these    compounds by hydrazinolysis, for example.

Most of the phenylacetyl halides, required for preparing the compounds(II), of the formula (XIV)

in which

-   W, X, Y and Z are as defined above-   and-   Hal represents fluorine, chlorine or bromine, preferably chlorine,

are known, or they can be prepared by known processes (WO 95/20572, EP-A668 267, WO 95/26954, WO 96/25395, WO 96/35664, WO 97/02243, WO97/01535, WO 97/36868, WO 98/05638, WO 99/43649, WO 99/48869, WO99/55673).

The compounds of the formulae (XVI) and (XV) are likewise known and canbe prepared by known processes (N. A. Porter et al. J. Org. Chem. 63,5547–5554, 1998).

Furthermore, acylhydroxylamino acid esters of the formula (II)

in which

-   A, B, D, W, X, Y, Z and R⁸ are as defined above, but where-   D is preferably not hydrogen    are obtained, for example, when phenylacetyl halides of the formula    (XIV)

in which

-   W, X, Y and Z are as defined above-   and-   Hal represents fluorine, chlorine or bromine, preferably chlorine,    are reacted with hydroxylamines of the formula (XVIII)

in which

-   D is as defined above, but is preferably not hydrogen,    to give compounds of the formula (XIX)

in which

-   D, W, X, Y and Z are as defined above,    and these compounds are then alkylated with haloalkyl esters of the    formula (XVI),

in which

-   A, B and R⁸ are as defined above-   and-   Hal represents chlorine, bromine and iodine, preferably bromine,    to give compounds of the formula (II) (E. K. Ryo et al., Bull.    Korean Chem. Soc. 20 965 (1999)).

Some of the compounds of the formula (XVIII) are commercially available,some are known, and they can be prepared by known processes.

Moreover, compounds of the formula (II) in which D is not hydrogen areobtained when compounds of the formula (II-a)

in which

-   A, B, W, X, Y, Z and R⁸ are as defined above    are alkylated with compounds of the formula (XX)    D-LG  (XX)    in which-   D is as defined above, but is not hydrogen,    and-   LG is a leaving group, such as, for example, chlorine, bromine,    iodine, mesylate, tosylate or triflate,    to give compounds of the formula II (see Example II-3).

Some of the compounds of the formula (XX) are commercially available,some are known, and they can be prepared by known processes.

The acid halides of the formula (III), carboxylic anhydrides of theformula (IV), chloroformic esters or chloroformic thioesters of theformula (V), chloromonothioformic esters or chlorodithioformic esters ofthe formula (VI), sulphonyl chlorides of the formula (VII), phosphoruscompounds of the formula (VIII) and metal hydroxides, metal alkoxides oramines of the formulae (IX) and (X), respectively, and isocyanates ofthe formula (XI) and carbamoyl chlorides of the formula (XII)furthermore required as starting materials for carrying out theprocesses (B), (C), (D), (E), (F), (G) and (H) according to theinvention are generally known compounds of organic or inorganicchemistry.

The process (A) is characterized in that compounds of the formula (II)in which A, B, D, W, X, Y, Z and R⁸ are as defined above are subjectedto an intramolecular condensation in the presence of a base.

Suitable diluents for use in the process (A) according to the inventionare all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methylpyrrolidone, andalso alcohols, such as methanol, ethanol, propanol, isopropanol,butanol, isobutanol and tert-butanol.

Suitable bases (deprotonating agents) for carrying out the process (A)according to the invention are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which can also be used in the presenceof phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltri(C₈–C₁₀)alkylammonium chloride) or TDA 1(=tris(methoxyethoxyethyl)amine). It is furthermore possible to usealkali metals, such as sodium or potassium. Also suitable are alkalimetal and alkaline earth metal amides and hydrides, such as sodiumamide, sodium hydride and calcium hydride, and furthermore also alkalimetal alkoxides, such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide.

When carrying out the process (A) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −78° C. and250° C., preferably between 0° C. and 150° C.

The process (A) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (A) according to the invention, thereaction components of the formula (II) and the deprotonating bases aregenerally employed in approximately double-equimolar amounts. However,it is also possible to use a relatively large excess (up to 3 mol) ofone component or the other.

The process (B-α) is characterized in that compounds of the formula(I-a) are in each case reacted with carbonyl halides of the formula(III), if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder.

Suitable for use as diluents in the process (B-α) according to theinvention are all solvents which are inert towards the acid halides.Preference is given to using hydrocarbons, such as benzine, benzene,toluene, xylene and tetraline, furthermore halogenated hydrocarbons,such as methylene chloride, chloroform, carbon tetrachloride,chlorobenzene and o-dichlorobenzene, moreover ketones, such as acetoneand methyl isopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such as dimethylsulphoxide and sulpholane. The hydrolytic stability of the acid halidepermitting, the reaction can also be carried out in the presence ofwater.

Acid binders suitable for the reaction according to process (B-α)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethylaniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, moreover alkali metal and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides, such as sodium hydroxideand potassium hydroxide.

When carrying out the process (B-α) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −20° C. and+150° C., preferably between 0° C. and 100° C.

When carrying out the process (B-α) according to the invention, thestarting materials of the formula (I-a) and the carbonyl halide of theformula (III) are generally each employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(up to 5 mol) of the carbonyl halide. Work-up is carried out bycustomary methods.

The process (B-β) is characterized in that compounds of the formula(I-a) are reacted with carboxylic anhydrides of the formula (IV), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

Diluents suitable for use in the process (B-β) according to theinvention are preferably those diluents which are also preferred whenacid halides are used. Besides, a carboxylic anhydride employed inexcess may simultaneously act as diluent.

Preferred acid binders which are, if appropriate, employed in process(B-β) are those acid binders which are also preferred when acid halidesare used.

When carrying out the process (B-β) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between −20° C. and+150° C., preferably between 0° C. and 100° C.

When carrying out the process (B-β) according to the invention, thestarting materials of the formula (I-a) and the carboxylic anhydride ofthe formula (IV) are generally each employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(up to 5 mol) of the carboxylic anhydride. Work-up is carried out bycustomary methods.

In general, diluent and excess carboxylic anhydride and the carboxylicacid formed are removed by distillation or by washing with an organicsolvent or with water.

The process (C) is characterized in that compounds of the formula (I-a)are in each case reacted with chloroformic esters or chloroformicthioesters of the formula (V), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

Acid binders suitable for the reacton of process (C) according to theinvention are all customary acid acceptors. Preference is given to usingtertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBA, Hünigbase and N,N-dimethylaniline, furthermore alkaline earth metal oxides,such as magnesium oxide and calcium oxide, moreover alkali metal andalkaline earth metal carbonates, such as sodium carbonate, potassiumcarbonate and calcium carbonate, and also alkali metal hydroxides, suchas sodium hydroxide and potassium hydroxide.

Diluents suitable for the process (C) according to the invention are allsolvents which are inert towards the chloroformic esters or chloroformicthioesters. Preference is given to using hydrocarbons, such as benzine,benzene, toluene, xylene and tetraline, furthermore halogenatedhydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, and also strongly polar solvents, such asdimethyl sulphoxide and sulpholane.

When carrying out the process (C) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ifthe process is carried out in the presence of a diluent and an acidbinder, the reaction temperatures are generally between −20° C. and+100° C., preferably between 0° C. and 50° C.

The process (C) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (C) according to the invention, thestarting materials of the formula (I-a) and the appropriate chloroformicester or chloroformic thioester of the formula (V) are generally eachemployed in approximately equivalent amounts. However, it is alsopossible to use a relatively large excess (up to 2 mol) of one componentor the other. Work-up is carried out by customary methods. In general,precipitated salts are removed and the reaction mixture that remains isconcentrated by removing the diluent.

The process (D) according to the invention is characterized in thatcompounds of the formula (I-a) are in each case reacted with compoundsof the formula (VI), in the presence of a diluent and, if appropriate,in the presence of an acid binder.

In the preparation process (D), about 1 mol of chloromonothioformicester or chlorodithioformic ester of the formula (VI) is reacted permole of starting material of the formula (I-a), at from 0 to 120° C.,preferably from 20 to 60° C.

Suitable diluents, which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, sulphones, sulphoxides, andalso halogenated alkanes.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-a)is prepared by addition of strong deprotonating agents, such as, forexample, sodium hydride or potassium tert-butoxide, the further additionof acid binders may be dispensed with.

If acid binders are used, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine or triethylamine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is by customary methods.

Process (E) according to the invention is characterized in thatcompounds of the formula (I-a) are in each case reacted with sulphonylchlorides of the formula (VII), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

In the preparation process (E), about 1 mol of sulphonyl chloride of theformula (VII) is reacted per mole of starting material of the formula(I-a), at from −20 to 150° C., preferably from 20 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, nitriles, sulphones,sulphoxides or halogenated hydrocarbons, such as methylene chloride.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-a)is prepared by addition of strong deprotonating agents (such as, forexample, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders may be dispensed with.

If acid binders are used, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine or triethylamine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is by customary methods.

The process (F) according to the invention is characterized in thatcompounds of the formula (I-a) are in each case reacted with phosphoruscompounds of the formula (VIII), if appropriate in the presence of adiluent and, if appropriate, in the presence of an acid binder.

In the preparation process (F), 1 to 2, preferably 1 to 1.3, mol of thephosphorus compound of the formula (VIII) are reacted per mole of thecompounds (I-a), at temperatures between −40° C. and 150° C., preferablybetween −10 and 110° C., to obtain compounds of the formula (I-e).

Suitable diluents, which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, nitriles, alcohols, sulphides,sulphones, sulphoxides, etc.

Preference is given to using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide or methylene chloride.

Suitable acid binders, which are added, if appropriate, are customaryinorganic or organic bases, such as hydroxides, carbonates or amines.Sodium hydroxide, sodium carbonate, potassium carbonate, pyridine andtriethylamine may be mentioned by way of example.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods of organic chemistry.Purification of the resulting end products is preferably bycrystallization, chromatographic purification or by “incipientdistillation”, i.e. removal of the volatile components under reducedpressure.

The process (G) is characterized in that compounds of the formula (I-a)are reacted with metal hydroxides or metal alkoxides of the formula (IX)or with amines of the formula (X), if appropriate in the presence of adiluent.

Preferred diluents for use in the process (G) according to the inventionare ethers, such as tetrahydrofuran, dioxane or diethyl ether, or elsealcohols, such as methanol, ethanol or isopropanol, and also water.

The process (G) according to the invention is generally carried outunder atmospheric pressure.

The reaction temperatures are generally between −20° C. and 100° C.,preferably between 0° C. and 50° C.

The process (H) according to the invention is characterized in thatcompounds of the forrmula (I-a) are in each case reacted with (H-α)compounds of the formula (XI), if appropriate in the presence of adiluent and if appropriate in the presence of a catalyst, or (H-β) withcompounds of the formula (XII), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

In preparation process (H-α), about 1 mol of isocyanate of the formula(XI) is reacted per mole of starting material of the formula (I-a), atfrom 0 to 100° C., preferably from 20 to 50° C.

Suitable diluents which are added, if appropriate, are all inert organicsolvents, such as ethers, amides, nitriles, sulphones, sulphoxides.

If appropriate, catalysts can be added to accelerate the reaction.Advantageously, the catalysts used are organotin compounds, such as, forexample, dibutyltin dilaurate. The process is preferably carried out atatmospheric pressure.

In the preparation process (H-β), about 1 mol of carbamoyl chloride ofthe formula (XII) is reacted per mole of starting material of theformula (I-a), at from −20 to 150° C., preferably from 0 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, sulphones, sulphoxides orhalogenated hydrocarbons.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound (I-a) isprepared by addition of strong deprotonating agents (such as, forexample, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders can be dispensed with.

If acid binders are used, these are customary organic or inorganicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, triethylamine or pyridine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The active compounds are suitable for protecting plants and plantorgans, for increasing the harvest yields, for improving the quality ofthe harvested goods and for controlling animal pests, in particularinsects, arachnids and nematodes, which are encountered in agriculture,in forests, in gardens and leisure facilities, in the protection ofstored products and of materials, and in the hygiene sector, and havegood plant tolerance, favourable toxicity to warm-blooded animals andgood environmental compatibility. They may be preferably employed asplant protection agents. They are active against normally sensitive andresistant species and against all or some stages of development. Theabovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorporis, Haematopinus spp., Linognathus spp., Trichodectes spp. andDamalinia spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofinannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumniferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis, Costelytra zealandica and Lissorhoptrusoryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the class of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Omithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., Brevipalpus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

If appropriate, the compounds according to the invention can, at certainconcentrations or application rates, also be used as herbicides ormicrobicides, for example as fungicides, antimycotics and bactericides.If appropriate, they can also be employed as intermediates or precursorsfor the synthesis of other active compounds.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and inclusive of the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offsets and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on the surroundings, environment or storage space bythe customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants, and/or foam-formers.

If the extender used is water, it is also possible to employ for exampleorganic solvents as auxiliary solvents. Essentially, suitable liquidsolvents are: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and also their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and alsowater.

As solid carriers there are suitable:

for example ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as highly disperse silica,alumina and silicates; as solid carriers for granules there aresuitable: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, and also syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;as emulsifiers and/or foam-formers there are suitable: for examplenonionic and anionic emulsifiers, such as polyoxyethylene fatty acidesters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand also protein hydrolysates; as dispersants there are suitable: forexample lignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be employed as suchor in their formulations as a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides in order forexample to increase the activity spectrum or avoid the development ofresistance. In many cases synergistic effects are achieved, ie. theefficacy of the mixture is greater than the efficacy of the individualcomponents.

Favourable examples of co-components in mixtures are the followingcompounds:

Fungicides:

aldimorph, ampropylfos, ampropylfos-potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

ediphenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropirnorph, fentin acetate, fentinhydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, flircarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazole,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations, such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxirn, oxyfenthiin,paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole,prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole,propineb, pyraclostrobin, pyrazophos, pyrifenox, pyrimethanil,pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,trifloxystrobin, triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamide, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

-   α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,-   α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,-   (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,-   (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,-   1-isopropyl    {2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,-   1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,-   1-(2-methyl-1-naphthalenyl)-1H-pyrrol-2,5-dione,-   1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidindione,-   1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,-   1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,-   1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,-   1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,-   1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,-   2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,-   2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,-   2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,-   2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,-   2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,-   2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,-   2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,-   2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,-   2-aminobutane,-   2-bromo-2-(bromomethyl)-pentanedinitrile,-   2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,-   2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,-   2-phenylphenol (OPP),-   3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrol-2,5-dione,-   3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,-   3-(1,1-dimethylpropyl)-1-oxo-1H-indene-2-carbonitrile,-   3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,-   4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,-   4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,-   8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,-   8-hydroxyquinoline sulphate,-   9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,-   bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,-   cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,-   cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine    hydrochloride,-   ethyl [(4-chlorophenyl)-azo]-cyanoacetate,-   potassium bicarbonate,-   methanetetrathiol-sodium salt,-   methyl    1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,-   methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,-   methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,-   N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,-   N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,-   N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,-   N-(6-methoxy)-3-pyridinyl-cyclopropanecarboxamide,-   N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,-   N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,-   N-formyl-N-hydroxy-DL-alanine-sodium salt,-   O,O-diethyl    [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,-   O-methyl S-phenyl phenylpropylphosphoramidothioate,-   S-methyl 1,2,3-benzothiadiazole-7-carbothioate,-   spiro[2H]-1-benzopyrane-2,1′(3′H)-isobenzofuran]-3′-one,-   4-[3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-acryloyl]-morpholine

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/acaricides/nematicides:

abamectin, acephate, acetamiprid, acequinocyl, acrinathrin, alanycarb,aldicarb, aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz,avermectin, AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphosM, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, bistrifluron,BPMC, bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim,butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, chromafenozide, cis-resmethrin, cispermethrin,clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, dicofol, diflubenzuron, dimethoate,dimethylvinphos, dinetofuran, diofenolan, disulfoton, docusat-sodium,dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthora spp.,esfenvalerate, ethiofencarb, ethion, ethiprole, ethoprophos, etofenprox,etoxazole, etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flumethrin, flupyrazofos, flutenzine, fluvalinate, fonophos,fosmethilan, fosthiazate, fubfenprox, furathiocarb,

granulosis viruses,

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,

imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses,

lambda-cyhalothrin, lufenuron,

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, metharhizium flavoviride, methidathion, methiocarb,methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone,mevinphos, milbemectin, milbemycin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron,

omethoate, oxamyl, oxydemethon M,

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,propargite, propoxur, prothiofos, prothoate, pymetrozine, pyraclofos,pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen,pyriproxyfen,

quinalphos,

ribavirin,

salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep,sulprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, tetradifon, theta-cypermethrin, thiacloprid,thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate,thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,

triarathene, triazamate, triazophos, triazuron, trichlophenidine,trichlorfon, triflumuron, trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii,

YI 5302,

zeta-cypermethrin, zolaprofos,

-   (1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,-   (3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,-   1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,-   2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,-   2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,-   2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,-   2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,-   3-methylphenyl propylcarbamate,-   4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,-   4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,-   4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,-   4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,-   Bacillus thuringiensis strain EG-2348,-   [2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,-   2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl    butanoate,-   [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,-   dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,-   ethyl    [2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,-   N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,-   N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,-   N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,-   N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,-   N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,-   O,O-diethyl-[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,-   N-cyanomethyl-4-trifluoromethyl-nicotinamide,-   3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridin-2-yloxy)-propoxy]-benzene.

It is also possible to admix other known active compounds, such asherbicides, or fertilizers and growth regulators, safeners andsemichemicals.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds, without it beingnecessary for the synergistic agent added to be active itself.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with inhibitors which reduce degradation of the activecompound after use in the vicinity of the plant, on the surface of partsof plants or in plant tissues.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompound is distinguished by an excellent residual action on wood andclay as well as by a good stability to alkali on limed substrates.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and plant cultivars obtained by genetic engineering, ifappropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are understood as meaning plants with novelproperties (“traits”) which are grown by conventional cultivation, bymutagenesis or by recombinant DNA techniques. These may be cultivars,biotypes or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possiblewhich exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably to be treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparted particularly advantageoususeful properties (“traits”) to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, tobacco, oilseed rape and also fruit plants (with thefruits apples, pears, citrus fruits and grapes), and particular emphasisis given to maize, soya beans, potatoes, cotton, tobacco and oilseedrape. Traits that are emphasized are in particular increased defence ofthe plants against insects, arachnids, nematodes and slugs and snails bytoxins formed in the plants, in particular those formed in the plants bythe genetic material from Bacillus thuringiensis (for example by thegenes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c,Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelowreferred to as “Bt plants”). Traits which are also particularlyemphasized are the increased resistance of plants to fungi, bacteria andviruses by systemic acquired resistance (SAR), systemin, phytoalexins,elicitors and resistance genes and the correspondingly expressedproteins and toxins. Traits that are furthermore particularly emphasizedare the increased tolerance of the plants to certain herbicidally activecompounds, for example imidazolinones, sulphonylureas, glyphosate orphosphinotricin (for example the “PAT” gene). The genes which impart thedesired traits in question can also be present in combination with oneanother in the transgenic plants. Examples of “Bt plants” which may bementioned are maize varieties, cotton varieties, soya bean varieties andpotato varieties which are sold under the trade names YIELD GARD® (forexample maize, cotton, soya beans), KnockOut® (for example maize),StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) andNewLeaf® (potato). Examples of herbicide-tolerant plants which may bementioned are maize varieties, cotton varieties and soya bean varietieswhich are sold under the trade names Roundup Ready® (tolerance toglyphosate, for example maize, cotton, soya bean), Liberty Link®(tolerance to phosphinotricin, for example oilseed rape), IMI®(tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, forexample maize). Herbicide-resistant plants (plants bred in aconventional manner for herbicide tolerance) which may be mentionedinclude the varieties sold under the name Clearfield® (for examplemaize). Of course, these statements also apply to plant cultivars havingthese genetic traits or genetic traits still to be developed, whichcultivars will be developed and/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the formula I orthe active compound mixtures according to the invention. The preferredranges stated above for the active compounds or mixtures also apply tothe treatment of these plants. Particular emphasis is given to thetreatment of plants with the compounds or mixtures specificallymentioned in the present text.

The active compounds according to the invention act not only againstplant, hygiene and stored product pests, but also in the veterinarymedicine sector against animal parasites (ectoparasites), such as hardticks, soft ticks, mange mites, leaf mites, flies (biting and licking),parasitic fly larvae, lice, hair lice, feather lice and fleas. Theseparasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

From the subclass of the Acari (acavids) and the orders of the Meta- andMesostigmata, for example, Argas spp., Omithodorus spp., Otobius spp.,Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Stemostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) und Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which infest agriculturalproductive livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese and bees, other pets, such as, for example, dogs, cats,caged birds and aquarium fish, and also so-called test animals, such as,for example, hamsters, guinea pigs, rats and mice. By controlling thesearthropods, cases of death and reduction in productivity (for meat,milk, wool, hides, eggs, honey etc.) should be diminished, so that moreeconomic and easier animal husbandry is possible by use of the activecompounds according to the invention.

The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of molded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

When used for cattle, poultry, pets and the like, the active compoundsof the formula (I) can be used as formulations (for example powders,emulsions, free-flowing compositions), which comprise the activecompounds in an amount of 1 to 80% by weight, directly or after 100 to10 000-fold dilution, or they can be used as a chemical bath.

It has furthermore been found that the compounds according to theinvention have a strong insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout a limitation:

Beetles, such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobiusmollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctusplanicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale,Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec., Dinoderus minutus.

Hymenopterons, such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites, such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,Coptotermes formosanus.

Bristletails, such as Lepisma saccharina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cards, leather, wood and processed wood products andcoating compositions.

Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

Wood and processed wood products which can be protected by the agentsaccording to the invention or mixtures comprising these are to beunderstood as meaning, for example:

building timber, wooden beams, railway sleepers, bridge components, boatjetties, wooden vehicles, boxes, pallets, containers, telegraph poles,wood panelling, wooden windows and doors, plywood, chipboard, joinery orwooden products which are used quite generally in house-building or inbuilding joinery.

The active compounds can be used as such, in the form of concentrates orgenerally customary formulations, such as powders, granules, solutions,suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersing agent and/or binder or fixing agent, awater repellent, if appropriate siccatives and UV stabilizers and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

The insecticidal compositions or concentrates used for the preservationof wood and wood-derived timber products comprise the active compoundaccording to the invention in a concentration of 0.0001 to 95% byweight, in particular 0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thenature and occurrence of the insects and on the medium. The optimumamount employed can be determined for the use in each case by a seriesof tests. In general, however, it is sufficient to employ 0.0001 to 20%by weight, preferably 0.001 to 10% by weight, of the active compound,based on the material to be preserved.

Solvents and/or diluents which are used are an organic chemical solventor solvent mixture and/or an oily or oil-like organic chemical solventor solvent mixture of low volatility and/or a polar organic chemicalsolvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

Organic chemical solvents which are preferably used are oily or oil-likesolvents having an evaporation number above 35 and a flashpoint above30° C., preferably above 45° C. Substances which are used as such oilyor oil-like water-insoluble solvents of low volatility are appropriatemineral oils or aromatic fractions thereof, or solvent mixturescontaining mineral oils, preferably white spirit, petroleum and/oralkylbenzene.

Mineral oils having a boiling range from 170 to 220° C., white spirithaving a boiling range from 170 to 220° C., spindle oil having a boilingrange from 250 to 350° C., petroleum and aromatics having a boilingrange from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-like solvents of low volatility which have anevaporation number above 35 and a flashpoint above 30° C., preferablyabove 45° C., can be replaced in part by organic chemical solvents ofhigh or medium volatility, provided that the solvent mixture likewisehas an evaporation number above 35 and a flashpoint above 30° C.,preferably above 45° C., and that the insecticide/fungicide mixture issoluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, some of the organic chemicalsolvent or solvent mixture or an aliphatic polar organic chemicalsolvent or solvent mixture is replaced. Aliphatic organic chemicalsolvents containing hydroxyl and/or ester and/or ether groups, such as,for example, glycol ethers, esters or the like, are preferably used.

Organic chemical binders which are used in the context of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se, are water-dilutable and/or are soluble or dispersible oremulsifiable in the organic chemical solvents employed, in particularbinders consisting of or comprising an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenolic resin, hydrocarbon resin, such as indene-cumarone resin,silicone resin, drying vegetable oils and/or drying oils and/orphysically drying binders based on a natural and/or synthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances canalso be used as binders in an amount of up to 10% by weight. Dyestuffs,pigments, water-repelling agents, odour correctants and inhibitors oranticorrosive agents and the like which are known per se canadditionally be employed.

It is preferred according to the invention for the composition orconcentrate to comprise, as the organic chemical binder, at least onealkyd resin or modified alkyd resin and/or one drying vegetable oil.Alkyd resins having an oil content of more than 45% by weight,preferably 50 to 68% by weight, are preferably used according to theinvention.

All or some of the binder mentioned can be replaced by a fixing agent(mixture) or a plasticizer (mixture). These additives are intended toprevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

The plasticizers originate from the chemical classes of phthalic acidesters, such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoricacid esters, such as tributyl phosphate, adipic acid esters, such asdi-(2-ethylhexyl)adipate, stearates, such as butyl stearate or amylstearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

Fixing agents are based chemically on polyvinyl alkyl ethers, such as,for example, polyvinyl methyl ether or ketones, such as benzophenone orethylenebenzophenone.

Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementioned organicchemical solvents or diluents, emulsifiers and dispersing agents.

Particularly effective preservation of wood is achieved by impregnationprocesses on a large industrial scale, for example vacuum, double vacuumor pressure processes.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

Possible additional mixing partners are, preferably, the insecticidesand fungicides mentioned in WO 94/29 268. The compounds mentioned inthis document are an explicit constituent of the present application.

Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, transfluthrin, thiacloprid,methoxyphenoxide, triflumuron, chlothianidin, spinosad, tefluthrin,

and also fungicides, such as epoxyconazole, hexaconazole, azaconazole,propiconazole, tebuconazole, cyproconazole, metconazole, imazalil,dichlorfluanid, tolylfluanid, 3-iodo-2-propinyl-butyl carbamate,N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

The compounds according to the invention can at the same time beemployed for protecting objects which come into contact with saltwateror brackish water, such as hulls, screens, nets, buildings, moorings andsignalling systems, against fouling.

Fouling by sessile Oligochaeta, such as Serpulidae, and by shells andspecies from the Ledamorpha group (goose barnacles), such as variousLepas and Scalpellum species, or by species from the Balanomorpha group(acorn barnacles), such as Balanus or Pollicipes species, increases thefrictional drag of ships and, as a consequence, leads to a markedincrease in operation costs owing to higher energy consumption andadditionally frequent residence in the dry dock.

Apart from fouling by algae, for example Ectocarpus sp. and Ceramiumsp., in particular fouling by sessile Entomostraka groups, which comeunder the generic term Cirripedia (cirriped crustaceans), is ofparticular importance.

Surprisingly, it has now been found that the compounds according to theinvention, alone or in combination with other active compounds, have anoutstanding antifouling action.

Using the compounds according to the invention, alone or in combinationwith other active compounds, allows the use of heavy metals such as, forexample, in bis(trialkyltin)sulphides, tri-n-butyltin laurate,tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride,tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenumdisulphide, antimony oxide, polymeric butyl titanate,phenyl-(bispyridine)bismuth chloride, tri-n-butyltin fluoride, manganeseethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol1-oxide, bisdimethyldithiocarbamoylzinc ethylene-bisthiocarbamate, zincoxide, copper(I) ethylene-bisdithiocarbamate, copper thiocyanate, coppernaphthenate and tributyltin halides to be dispensed with, or theconcentration of these compounds to be substantially reduced.

If appropriate, the ready-to-use antifouling paints can additionallycomprise other active compounds, preferably algicides, fungicides,herbicides, molluscicides, or other antifouling active compounds.

Preferably suitable components in combinations with the antifoulingcompositions according to the invention are:

algicides such as

2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,dichlorophen, diuron, endothal, fentin acetate, isoproturon,methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

fungicides such as

benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide,dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate,tolylfluanid and azoles such as

azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole,propiconazole and tebuconazole;

molluscicides such as

fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb andtrimethacarb, Fe-chelate;

or conventional antifouling active compounds such as

4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulphone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium,copper, sodium and zinc salts of 2-pyridinethiol 1-oxide,pyridine-triphenylborane, tetrabutyldistannoxane,2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine,2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulphide and2,4,6-trichlorophenylmaleimide.

The antifouling compositions used comprise the active compound accordingto the invention of the compounds according to the invention in aconcentration of 0.001 to 50% by weight, in particular 0.01 to 20% byweight.

Moreover, the antifouling compositions according to the inventioncomprise the customary components such as, for example, those describedin Ungerer, Chem. Ind. 1985, 37, 730–732 and Williams, AntifoulingMarine Coatings, Noyes, Park Ridge, 1973.

Besides the algicidal, fungicidal, molluscicidal active compounds andinsecticidal active compounds according to the invention, antifoulingpaints comprise, in particular, binders.

Examples of recognized binders are polyvinyl chloride in a solventsystem, chlorinated rubber in a solvent system, acrylic resins in asolvent system, in particular in an aqueous system, vinyl chloride/vinylacetate copolymer systems in the form of aqueous dispersions or in theform of organic solvent systems, butadiene/styrene/acrylonitrilerubbers, drying oils such as linseed oil, resin esters or modifiedhardened resins in combination with tar or bitumens, asphalt and epoxycompounds, small amounts of chlorine rubber, chlorinated polypropyleneand vinyl resins.

If appropriate, paints also comprise inorganic pigments, organicpigments or colorants which are preferably insoluble in salt water.Paints may furthermore comprise materials such as colophonium to allowcontrolled release of the active compounds. Furthermore, the paints maycomprise plasticizers, modifiers which affect the rheological propertiesand other conventional constituents. The compounds according to theinvention or the abovementioned mixtures may also be incorporated intoself-polishing antifouling systems.

The active compounds are also suitable for controlling animal pests, inparticular insects, arachnids and mites, which are found in enclosedspaces such as, for example, dwellings, factory halls, offices, vehiclecabins and the like. They can be employed alone or in combination withother active compounds and auxiliaries in domestic insecticide productsfor controlling these pests. They are active against sensitive andresistant species and against all developmental stages. These pestsinclude:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga camaria, Simulium spp., Stomoxyscalcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

In the field of household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricacid esters, carbamates, pyrethroids, neonicotinoids, growth regulatorsor active compounds from other known classes of insecticides.

They are used in aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free or passive evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

The active compounds according to the invention can also be used asdefoliants, desiccants, haulm killers and, especially, as weedkillers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The active compounds according to the invention are suitable, dependingon the concentration, for the total control of weeds, for example onindustrial terrain and rail tracks, and on paths and areas with andwithout tree plantings. Similarly, the active compounds according to theinvention can be employed for controlling weeds in perennial crops, forexample forests, decorative tree plantings, orchards, vineyards, citrusgroves, nut orchards, banana plantations, coffee plantations, teaplantations, rubber plantations, oil palm plantations, cocoaplantations, soft fruit plantings and hop fields, on lawns, turf andpastureland, and for the selective control of weeds in annual crops.

The compounds of the formula (I) according to the invention have strongherbicidal activity and a broad active spectrum when used on the soiland on above-ground parts of plants. To a certain extent they are alsosuitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothby the pre-emergence and by the post-emergence method.

At certain concentrations or application rates, the active compoundsaccording to the invention can also be employed for controlling animalpests and fungal or bacterial plant diseases. If appropriate, they canalso be used as intermediates or precursors for the synthesis of otheractive compounds.

The active compounds can be converted into the customary formulationssuch as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and microencapsulations in polymeric materials.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents and/orsolid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants, and/or foam formers.

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

Suitable solid carriers are: for example ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticmaterials such as finely divided silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates,or else protein hydrolysates; suitable dispersants are: for examplelignosulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic colorants suchas alizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in their formulations, can also be used as mixtures withknown herbicides and/or substances which improve the compatibility withcrop plants (“safeners”), finished formulations or tank mixes beingpossible. Also possible are mixtures with weed-killers comprising one ormore known herbicides and a safener.

Possible components for the mixtures are known herbicides, for example

acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuiron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin(-ethyl), benfuresate, bensulfuron (-methyl), bentazone, benzfendizone,benzobicyclon, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox,bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor,butafenacil (-allyl), butroxydim, butylate, cafenstrole, caloxydim,carbetamide, carfentrazone (-ethyl), chlomethoxyfen, chloramben,chloridazon, chlorimuron (-ethyl), chlomitrofen, chlorsulfuron,chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim,clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid,clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl),2,4-D, 2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P),diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb,ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop (-P-ethyl), fentrazamide,flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam,fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet,flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn,flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl),flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl), flurprimidol,flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron,glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen,haloxyfop (-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin,imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil,isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop,mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron,metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron,metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide,napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin,oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen,paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone,phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron(-methyl), profluazol, prometryn, propachlor, propanil, propaquizafop,propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb,prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol,pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr,tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl),tritosulfuron.

Furthermore suitable for the mixtures are known safeners, for example:

AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D,DKA-24, dichlormid, dymron, fenclorim, fenchlorazol (-ethyl), flurazole,fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P),mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292, R-29148.

A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

The active compounds according to the invention can be applied bothbefore and after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the amounts used are between 1 g and 10 kg of active compoundper hectare of soil surface, preferably between 5 g and 5 kg per ha.

The substances according to the invention have potent microbicidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.gramiriea

(conidia form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus

(conidia form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae; and

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The active compounds according to the invention also have very goodfortifying action in plants. Accordingly, they can be used formobilizing the defences of the plant against attack by undesirablemicroorganisms.

In the present context, plant-fortifying (resistance-inducing)substances are to be understood as meaning those substances which arecapable of stimulating the defence system of plants such that, when thetreated plants are subsequently inoculated with undesirablemicroorganisms, they show substantial resistance against thesemicroorganisms.

In the present case, undesirable microorganisms are to be understood asmeaning phytopathogenic fungi, bacteria and viruses. Accordingly, thesubstances according to the invention can be used to protect plants fora certain period after the treatment against attack by the pathogensmentioned. The period for which protection is provided generally extendsover 1 to 10 days, preferably 1 to 7 days, after the treatment of theplants with the active compounds.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The active compounds according to the invention are also suitable forincreasing the yield of crops. In addition, they show reduced toxicityand are well tolerated by plants.

At certain concentrations and application rates, the active compoundsaccording to the invention can also be used as herbicides, forinfluencing plant growth and for controlling animal pests. Ifappropriate, they can also be used as intermediates and precursors forthe synthesis of further active compounds.

In the protection of materials, the compounds according to the inventioncan be employed for protecting industrial materials against infectionwith, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be adhesives, sizes, paper and board, textiles, leather,wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably adhesives, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes), and against slime organismsand algae.

Microorganisms of the following genera may be mentioned as examples:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa, and

Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted into the customary formulations, suchas solutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Essentially,suitable liquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide and dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates, or else proteinhydrolysates. Suitable dispersants are: for example lignosulphite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such orin their formulations, also in a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum or to prevent development of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Examples of suitable mixing components are the following:

Fungicides:

2-phenylphenol; 8-hyroxyquinoline sulphate; acibenzolar-S-methyl;aldimorph; amidoflumet; ampropylfos; ampropylfos-potassium; andoprim;anilazine; azaconazole; azoxystrobin; benalaxyl; benodanil; benomyl;benthiavalicarb-isopropyl; benzamacril; benzamacril-isobutyl; bilanafos;binapacryl; biphenyl; bitertanol; blasticidin-S; bromuconazole;bupirimate; buthiobate; butylamine; calcium polysulphide; capsimycin;captafol; captan; carbendazim; carboxin; carpropamide; carvone;quinomethionate; chlobenthiazone; chlorfenazole; chloroneb;chlorothalonil; chlozolinate; clozylacon; cyazofamide; cyflufenamide;cymoxanil; cyproconazole; cyprodinil; cyprofuram; dagger G; debacarb;dichlofluanid; dichlone; dichlorophen; diclocymet; diclomezine;dicloran; diethofencarb; difenoconazole; diflumetorim; dimethirimol;dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap;diphenylamine; dipyrithione; ditalimfos; dithianon; dodine; drazoxolon;edifenphos; epoxiconazole; ethaboxarn; ethirimol; etridiazole;famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole; fenfuram;fenhexamide; fenitropan; fenoxanil; fenpiclonil; fenpropidin;fenpropimorph; ferbam; fluazinam; flubenzimine; fludioxanil; flumetover;flumorph; fluoromide; fluoxastrobin; fluquinconazole; flurprimidol;flusilazole; flusulfamide; flutolanil; flutriafol; folpet;fosetyl-aluminium; fosetyl-sodium; fuberidazole; furalaxyl; furametpyr;furcarbanil; furnecyclox; guazatine; hexachlorobenzene; hexaconazole;hymexazole; imazalil; imibenconazole; iminoctadine triacetate;iminoctadine tris-albesil; iodocarb; ipconazole; iprobenfos; iprodione;iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin;kresoxim-methyl; mancozeb; maneb; meferimzone; mepanipyrim; mepronil;metalaxyl; metalaxyl-M; metconazole; methasulfocarb; methfuroxam;metiram; metominostrobin; metsulfovax; mildiomycin; myclobutanil;myclozolin; natamycin; nicobifen; nitrothal-isopropyl; noviflumuron;nuarimol; ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole;oxycarboxin; oxyfenthiin; paclobutrazole; pefurazoate; penconazole;pencycuron; phosdiphen; phthalide; picoxystrobin; piperalin; polyoxins;polyoxorim; probenazole; prochloraz; procymidone; proparnocarb;propanosine-sodium; propiconazole; propineb; proquinazid;prothioconazole; pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil;pyroquilon; pyroxyfur; pyrrolnitrine; quinconazole; quinoxyfen;quintozene; simeconazole; spiroxamine; sulphur; tebuconazole;tecloftalam; tecnazene; tetcyclacis; tetraconazole; thiabendazole;thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid;tolclofos-methyl; tolylfluanid; triadimefon; triadimenol; triazbutil;triazoxide; tricyclamide; tricyclazole; tridemorph; trifloxystrobin;triflumizole; triforine; triticonazole; uniconazole; validamycin A;vinclozolin; zineb; ziram; zoxamide;(2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide;1-(1-naphthalenyl)-1H-pyrrole-2,5-dione;2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine;2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide,2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide;3,4,5-trichloro-2,6-pyridinedicarbonitrile; Actinovate;cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol; methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate;monopotassium carbonate;N-(6-methoxy-3-pyridinyl)cyclopropanecarboxamide;N-butyl-8-(1,1-dimethylethyl)-1-oxaspiro[4.5]decan-3-amine; sodiumtetrathiocarbonate;

and copper salts and copper preparations, such as Bordeaux mixture;copper hydroxide; copper naphthenate; copper oxychloride; coppersulphate; cufraneb; cuprous oxide; mancopper; oxine-copper.

Bactericides:

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/acaricides/nematicides:

abamectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole,acrinathrin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb,aldoxycarb, allethrin, allethrin 1R-isomers, alpha-cypermethrin(alphamethrin), amidoflumet, aminocarb, amitraz, avermectin, AZ-60541,azadirachtin, azamethiphos, azinphos-methyl, azinphos-ethyl,azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, Bacillus thuringiensis strain EG-2348, Bacillusthuringiensis strain GC-91, Bacillus thuringiensis strain NCTC-11821,baculoviruses, Beauveria bassiana, Beauveria tenella, bendiocarb,benfuracarb, bensultap, benzoximate, beta-cyfluthrin, beta-cypermethrin,bifenazate, bifenthrin, binapacryl, bioallethrin,bioallethrin-S-cyclopentyl-isomer, bioethanomethrin, biopermethrin,bioresmethrin, bistrifluron, BPMC, brofenprox, bromophos-ethyl,bromopropylate, bromfenvinfos (-methyl), BTG-504, BTG-505, bufencarb,buprofezin, butathiofos, butocarboxim, butoxy-carboxim, butylpyridaben,

cadusafos, camphechlor, carbaryl, carbofuran, carbophenothion,carbosulfan, cartap, CGA-50439, quinomethionate, chlordane,chlordimeform, chloethocarb, chlorethoxyfos, chlorfenapyr,chlorfenvinphos, chlorfluazuron, chlormephos, chlorobenzilate,chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos (ethyl),chlovaporthrin, chromafenozide, cis-cypermethrin, cis-resmethrin,cis-permethrin, clocythrin, cloethocarb, clofentezine, clothianidine,clothiazoben, codlemone, coumaphos, cyanofenphos, cyanophos, cycloprene,cycloprothrin, cydia pomanella, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyphenothrin (1R-trans-isomer), cyromazine,

DDT, deltamethrin, demeton-S-methyl, demeton-S-methylsulphon,diafenthiuron, dialifos, diazinon, dichlofenthion, dichlorvos, dicofol,dicrotophos, dicyclanil, diflubenzuron, dimethoate, dimethylvinphos,dinobuton, dinocap, dinetefuran, diofenolan, disulfoton, docusat-sodium,dofenapyn, DOWCO-439,

eflusilanate, emamectin, emamectin-benzoate, empenthrin (1R-isomer),endosulfan, Entomopthora spp., EPN, esfenvalerate, ethiofencarb,ethiprole, ethion, ethoprophos, etofenprox, etoxazole, etrimfos,

famphur, fenamiphos, fenazaquin, fenbutatin oxide, fenfluthrin,fenitrothion, fenobucarb, fenothiocarb, fenoxacrim, fenoxycarb,fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fensulfothion,fenthion, fentrifanil, fenvalerate, fipronil, flonicamide, fluacrypyrim,fluazuron, flubenzimine, flubrocythrinate, flucycloxuron, flucythrinate,flufenerim, flufenoxuron, flufenprox, flumethrin, flupyrazofos,flutenzin (flufenzine), fluvalinate, fonofos, fonnetanate, formothion,fosmethilan, fosthiazate, fubfenprox (fluproxyfen), furathiocarb,

Gamma-HCH, gossyplure, grandlure, granulosis viruses,

halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron,hexythiazox, hydramethylnone, hydroprene,

IKA-2002, imidacloprid, imiprothrin, indoxacarb, iodofenphos,iprobenfos, isazofos, isofenphos, isoprocarb, isoxathion, ivermectin,

japonilure,

kadethrin, nuclear polyhedrosis viruses, kinoprene,

lambda-cyhalothrin, lindane, lufenuron,

malathion, mecarbam, mesulfenfos, metaldehyde, metam-sodium,methanacrifos, methamidophos, Metharhizium anisopliae, Metharhiziumflavoviride, methidathion, methiocarb, methomyl, methoprene,methoxychlor, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos, moxidectin,MTI-800,

naled, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide, nicotine,nitenpyram, nithiazine, NNI-0001, NNI-0101, NNI-0250, NNI-9768,novaluron, noviflumuron,

OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, omethoate, oxamyl,oxydemeton-methyl,

Paecilomyces fumosoroseus, parathion-methyl, parathion(-ethyl),permethrin (cis-, trans-), petroleum, PH-6045, phenothrin. (IR-transisomer), phenthoate, phorate, phosalone, phosmet, phosphamidon,phosphocarb, phoxim, piperonyl butoxide, pirimicarb, pirimiphos-methyl,pirimiphos-ethyl, prallethrin, profenofos, promecarb, propaphos,propargite, propetamphos, propoxur, prothiofos, prothoate,protrifenbute, pymetrozine, pyraclofos, pyresmethrin, pyrethrum,pyridaben, pyridalyl, pyridaphenthion, pyridathion, pyrimidifen,pyriproxyfen,

quinalphos,

resmethrin, RH-5849, ribavirin, RH-12457, RH-15525,

S-421, S-1833, salithion, sebufos, S1-0009, silafluofen, spinosad,spirodiclofen, spiromesifen, sulfluramide, sulfotep, sulprofos, S21-121,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimfos,teflubenzuron, tefluthrin, temephos, temivinphos, terbarn, terbufos,tetrachlorvinphos, tetradifon, tetramethrin, tetramethrin (1R-isomer),tetrasul, theta-cypermethrin, thiacloprid, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thiometon, thiosultap-sodium, thuringiensin, tolfenpyrad, tralocythrin,tralomethrin, transfluthrin, triarathene, triazamate, triazophos,triazuron, trichlophenidine, trichlorfon, triflumuron, trimethacarb,

vamidothion, vaniliprole, verbutin, Verticillium lecanii,

WL-108477, WL-40027,

YI-5201, YI-5301, YI-5302,

XMC, xylylcarb,

ZA-3274, zeta-cypermethrin, zolaprofos, ZXI-8901,

the compound 3-methylphenyl propylcarbamate (Tsumacide Z),

the compound3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]-octane-3-carbonitrile(CAS-Reg. No. 185982-80-3) and the corresponding 3-endo isomer (CAS-Reg.No. 185984-60-5) (cf. WO-96/37494, WO-98/25923),

and preparations comprising insecticidally active plant extracts,nematodes, fungi or viruses.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, is also possible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi (for example against Candida species,such as Candida albicans, Candida glabrata), and Epidermophytonfloccosum, Aspergillus species, such as Aspergillus niger andAspergillus fumigatus, Trichophyton species, such as Trichophytonmentagrophytes,

Microsporon species such as Microsporon canis and audouinii. The list ofthese fungi by no means limits the mycotic spectrum covered, but is onlyfor illustration.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is furthermore possible to apply the activecompounds by the ultra-low-volume method, or to inject the activecompound preparation or the active compound itself into the soil. It isalso possible to treat the seeds of the plants.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. For the treatment of partsof plants, the active compound application rates are generally between0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. For seeddressing, the active compound application rates are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For the treatment of the soil, the active compoundapplication rates are generally between 0.1 and 10,000 g/ha, preferablybetween 1 and 5000 g/ha.

The preparation and the use of the active compounds according to theinvention are illustrated by the examples below.

PREPARATION EXAMPLES Example I-a-1

0.79 g (20 mmol) of 60% sodium hydride is initially charged in anhydrousDMF. At room temperature, 3.13 g (9 mmol) of the compound of ExampleII-1 in a little DMF are added dropwise. The mixture is stirred at roomtemperature overnight.

The reaction mixture is poured into ice-water, acidified with conc.hydrochloric acid and extracted with dichloromethane, and the organicphase is separated off and concentrated. The residue is purified bysilica gel column chromatography (dichloromethane/methanol, 30:1).

Yield: 0.95 g (34% of theory), m.p. 69° C.

Analogously to Example I-a-1 and in accordance with the generalstatements, the following compounds of the formula (I-a) are obtained:

(I-a)

Ex. No. W X Y Z D A B m.p. ° C. I-a-2 H CH₃ 4-OCH₃ 5-CH₃ CH₃ CH₃ CH₃137–138 I-a-3 H CH₃ 4-CH₃ H CH₃ CH₃ CH₃ 110 I-a-4 Cl Cl 4-CF3 H CH₃ CH₃CH₃ 163 I-a-5 H CH₃ 4-CH₃ 5-CH₃ CH₃ CH₃ CH₃ 104 I-a-6 H CH₃ H5-(4-Cl—C₆H₄) CH₃ —(CH₂)₃— 162 I-a-7 H CH₃ H 5-(4-Cl—C₆H₄) CH₃ CH₃ CH₃153 I-a-8 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ CH₃ 110 I-a-9 CH₃ CH₃ 4-Br H CH₃ CH₃CH₃ 181 I-a-10 H Cl H 5-(4-Cl—C₆H₄) CH₃ —(CH₂)₃— 160 I-a-11 CH₃ CH₃4-CH₃ 3-CH₃ CH₃ CH₃ CH₃ 161 I-a-12 H Cl H 5-(4-Cl—C₆H₄) CH₃ CH₃ CH₃  143.5 I-a-13 CH₃ CH₃ 4-CH₃ H CH₃ —(CH₂)₄— 163 I-a-14 C₂H₅ CH₃ 4-Br HCH₃ CH₃ CH₃ 188 I-a-15 H CH₃ 4-Br 5-CH₃ CH₃ CH₃ CH₃ 112 I-a-16 H Br4-CH₃ 5-CH₃ CH₃ CH₃ CH₃ 117

Example I-a-17

1.0 g (3.27 mmol) of the compound of Example II-10 and a spatula tip ofanhydrous sodium acetate in 10 ml of acetic anhydride are heated underreflux overnight. 20 ml of water are added, the mixture is extractedtwice with CH₂Cl₂ and the extract is washed with NaHCO₃ solution, driedover MgSO₄ and concentrated. The residue is triturated with cyclohexaneand the resulting solid is filtered off and discarded. The filtrate isconcentrated. This gives the N,O-diacetate of the title compound whichis immediately hydrolysed.

Yield: 0.534 g (43.9% of theory)

0.17 g (0.46 mmol) of the diacetate and 0.04 g (1 mmol) of NaOH in 1 mlof ethanol are stirred at room temperature overnight. The mixture ispoured into water and extracted twice with CH₂Cl₂ and the extract isdried over MgSO₄ and concentrated. The residue crystallizes partiallyand is triturated with hexane. The resulting solid is filtered off.

Yield: 13 mg (10% of theory)

Melting point: 127° C.

Example I-b-1

0.32 g (1,09 mmol) of the compound of Example I-a-11 is initiallycharged in 5 ml of CH₂Cl₂, and 0.11 g (1.09 mmol) of triethylamine isadded. 0.12 g (1.09 mmol) of isobutyryl chloride is added. The mixtureis stirred under reflux overnight and then washed with 1N hydrochloricacid. The organic phase is dried and the solvent is distilled off. Theresidue is chromatographed on silica gel using cyclohexane/ethyl acetate10:3.

Yield: 0.297 g (75.8% of theory)

Melting point: 53° C.

The following compounds of the formula (I-b) are obtained analogously toExample 1-b-1 and in accordance with the general statements:

(I-b)

Ex. No. W X Z Y D A B L R¹ m.p. ° C. I-b-2 H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃CH₃ O (CH₃)₂CH 93.5

Example I-c-1

0.3 g (0.84 mmol) of the compound of Example I-a-7 initially charged in5 ml of CH₂Cl₂, and 0.08 g (0.84 mmol) of triethylamine is added. 0.11 g(0.84 mmol) of isobutyl chloroformate in anhydrous CH₂Cl₂ is addeddropwise at room temperature. The mixture is stirred under reflux. Afterthe reaction has ended, the mixture is washed with diluted hydrochloricacid, the organic phase is dried and the solvent is distilled off.

Yield: 0.28 g (74% of theory)

The following compounds of the formula (I-c) are obtained analogously toExample I-c-1 and in accordance with the general statements

(I-c)

Ex. No. W X Z Y D A B L M R² m.p. ° C. I-c-2 CH₃ CH₃ 3-CH₃ 4-CH₃ CH₃ CH₃CH₃ O O (CH₃)₂CH—CH₂ oil I-c-3 H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃ CH₃ O OC₂H₅— oil I-c-4 H CH₃ 5-(4-Cl—C₆H₄) H CH₃ —(CH₂)₃— O O C₂H₅— oil I-c-5 HCl 5-(4-Cl—C₆H₄) H CH₃ CH₃ CH₃ O O (CH₃)₂CH—CH₂ oil I-c-6 H Cl5-(4-Cl—C₆H₄) H CH₃ —(CH₂)₃— O O —(CH₂)₃— oil I-c-7 H Cl 5-(4-Cl—C₆H₄) HCH₃ —(CH₂)₃— O O (CH₃)₂CH—CH₂ oil

Example II-1

4 g (17 mmol) of the compound of Example XIX-1 and 4 g (20.5 mmol) ofethyl bromoisobutyrate are initially charged in anhydrous acetone, and2.8 g (20.5 mmol) of potassium carbonate are added. The mixture isstirred at 40° C. for 8 h. The mixture is filtered and the filtrate isconcentrated. The residue is taken up in dichloromethane and the organicphase is washed with water and brine, dried and concentrated.

Yield: 4.295 g (72% of theory).

¹H-NMR (400 MHz, CDCl₃): δ (ppm)=1.32; t; 3H; J=6.7 Hz, (CH₂—CH₃ ) 1.58;s; 6H; (2×CH₃ ); 3.22; s; 3H; (N—CH₃ ); 3.91; s; 2H; (—CH₂—); 4.25; q;J=6.7 Hz; 2H (O—CH₂—); 7.2; m; 2H (arom. H); 7.39; m; 1H (arom. H).

Example II-2

0.74 g (5 mmol) of the compound of Example XIII-1 and 0.44 g (5.5 mmol)of pyridine are together initially charged in anhydrous dichloromethane,at 0° C. 1.6 g (5.5 mmol) of 2,6-dichloro-4-trifluoromethylphenylacetylchloride are added. The reaction mixture is stirred at room temperatureovernight and then poured into water and washed with dilute sulphuricacid, and the organic phase is separated off and concentrated. Theresidue is triturated with hexane and the solid is filtered off withsuction.

Yield: 1.62 g (80% of theory), m.p. 152° C.

Example II-3

At room temperature, 0.1 g of sodium hydride is initially charged in 5ml of anhydrous DMF in a stirred three-necked flask fitted withhigh-performance condenser and thermometer. 0.89 g (1.99 mmol) of thecompound of Example II-2, dissolved in 10 ml of anhydrous DMF, is addeddropwise. The mixture is stirred for 10 min. 0.31 g (2.19 mmol) ofmethyl iodide is then added dropwise. The mixture is stirred at roomtemperature overnight. The reaction solution is poured into 50 ml ofice-water and extracted with 20 ml of dichloromethane, and the organicphase is dried and concentrated.

Yield: 0.78 g (94% of theory).

¹H-NMR (CDCl₃); δ (ppm)=1.35; t; J=7 Hz (OCH₂—CH₃); 1.63; s; 6H;(2×—CH₃), 3.23; s; 3H; (N—CH₃); 4.22; s; 2H; (—CH₂—); 4.28; q; J=7 Hz;2H (O—CH₂ —CH₃); 7.58; s; 2H (arom. H).

Analogously to Examples II-1 to II-3 and in accordance with the generalstatements on the preparation, the following compounds of the formula(II) are obtained:

(II)

Ex. No. W X Y Z D A B m.p. ° C. II-4 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ CH₃ oilII-5 H CH₃ H 5-(4-Cl—C₆H₄) CH₃ CH₃ CH₃ oil II-6 H CH₃ 4-OCH₃ 5-CH₃ CH₃CH₃ CH₃ oil II-7 H CH₃ 4-CH₃ H H CH₃ CH₃  76 II-8 CH₃ CH₃ 4-Br H H CH₃CH₃ 147 II-9 H CH₃ H 5-(4-Cl—C₆H₄) H CH₃ CH₃  78 II-10 H Cl 4-Cl H H CH₃CH₃  94 II-11 H CH₃ 4-CH₃ 5-CH₃ H CH₃ CH₃ 110 II-12 H CH₃ 4-CH₃ H Hi-C₃H₇ H  71 II-13 H CH₃ 4-CH₃ H CH₃ CH₃ CH₃ oil II-14 H CH₃ 4-CH₃ 5-CH₃CH₃ CH₃ CH₃ oil II-15 CH₃ CH₃ 4-Br H CH₃ CH₃ CH₃ oil II-16 H CH₃ 4-CH₃ HCH₂—O—C₂H₅ CH₃ CH₃ oil II-17 CH₃ CH₃ 4-CH₃ H H —(CH₂)₄—  95 II-18 CH₃CH₃ 4-CH₃ H CH₃ —(CH₂)₄— oil II-19 CH₃ CH₃ 4-CH₃ H H —(CH₂)₃— 115 II-20CH₃ CH₃ 4-CH₃ H CH₃ —(CH₂)₃— oil II-21 CH₃ CH₃ 4-Cl H H CH₃ CH₃ 116II-22 CH₃ CH₃ 4-Cl H CH₃ CH₃ CH₃ oil II-23 C₂H₅ CH₃ 4-Br H H CH₃ CH₃  119.5 II-24 C₂H₅ CH₃ 4-Br H CH₃ CH₃ CH₃ oil II-25 H Br 4-CH₃ 5-CH₃ HCH₃ CH₃ 120 II-26 H Br 4-CH₃ 5-CH₃ CH₃ CH₃ CH₃ oil II-27 H CH₃ 4-Br5-CH₃ H CH₃ CH₃ 127 II-28 H CH₃ 4-Br 5-CH₃ CH₃ CH₃ CH₃ oil II-29 CH₃ CH₃4-Br 3-CH₃ H CH₃ CH₃ 150 II-30 CH₃ CH₃ 4-Br 3-CH₃ CH₃ CH₃ CH₃ oil II-31H CH₃ H 5-(4-Cl—C₆H₄) H —(CH₂)₃— 133 II-32 H CH₃ H 5-(4-Cl—C₆H₄) CH₃—(CH₂)₃— oil II-33 H Cl H 5-(4-Cl—C₆H₄) H —(CH₂)₃— 120 II-34 H Cl H5-(4-Cl—C₆H₄) CH₃ —(CH₂)₃— oil

Example XIII-1

141 g (511 mmol) of the compound of Example XVII-1 are initially chargedin 1000 ml of methanol and 1000 ml of dichloromethane. 65 g of hydrazinehydrate are added. The mixture is stirred under reflux for 3 h. Themixture is cooled and the solid is filtered off with suction and washedwith dichloromethane. 5 l of 5% strength Na₂CO₃ solution are added, andthe mixture is extracted 5 times with dichloromethane. The organic phaseis dried and concentrated. The residue is distilled under high vacuum.

Yield: 64 g (85% of theory);

Boiling point: 40° C./0.55 mbar

Analogously to Example XIII-1 and in accordance with the generalstatements on the preparation, the following compounds of the formulaXIII are obtained:

(XIII)

Ex. No. A B R⁸ b.p. ° C./mbar XIII-2 —(CH₂)₄— C₂H₅ 48–55/52 XIII-3i-C₃H₇ H C₂H₅ 114/60 XIII-4 —(CH₂)₃— C₂H₅

Example XVIII-1

100 g of N-hydroxphthalimide and 119 g of bromoisobutyrate are togetherinitially charged in 1000 ml of anhydrous DMF in a stirred three-neckedflask fitted with high-performance condenser and thermometer. 62 g oftriethylamine are added, and the mixture is stirred at 60° C. for 28 h.The reaction mixture is poured into 500 ml of water and extracted 4times with 150 ml of MTBE, the organic phase is dried and concentratedand the residue is triturated with hexane. The solid is filtered offwith suction.

Yield: 141 g (83% of theory); m.p. 80° C.

The following compounds of the formula (XVII) are obtained analogouslyto Example XVII-1 and in accordance with the general statements on thepreparation:

(XVII)

Ex. No. A B R⁸ m.p. ° C. XVII-2 —(CH₂)₄— C₂H₅  83 XVII-3 i-C₃H₇ H C₂H₅oil XVII-4 —(CH₂)₃— C₂H₅ 109

Example XIX-1

At room temperature, 5.3 g (23 mol) of 2,4-dichlorophenylacetyl chlorideand 1.98 g (23 mol) of N-methylhydroxylamine hydrochloride are initiallycharged in anhydrous dichloromethane. 4.8 g of triethylamine are slowlyadded dropwise. The mixture is stirred at room temperature overnight andthen washed with dilute hydrochloric acid and with NaHCO₃ solution. Theorganic phase is dried and concentrated and the solid is taken up inMTBE and washed with dilute hydrochloric acid. The organic phase isdried and concentrated.

Yield: 4.12 g (74% of theory); m.p. 103° C.

Analogously to Example XIX-1 and in accordance with the generalstatements of the preparation, the following examples of the formula(XIX) are obtained:

(XIX)

Ex. No. W X Y Z D m.p. ° C. XIX-2 CH₃ CH₃ 4-CH₃ H CH₃ 130 XIX-3 H CH₃ H5-(4-Cl—C₆—H₄) CH₃ oil XIX-4 H CH₃ 4-OCH₃ 5-CH₃ CH₃ 115

Example A

Myzus Test

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) which are heavily infested by thepeach aphid (Myzus persicae) are treated by being dipped into thepreparation of active compound of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshas been killed.

In this test, for example, the following compound of the preparationexamples shows good activity:

TABLE A Plant-damaging insects Myzus test Concentration of activecompound Kill rate Active compounds in ppm in % after 6^(d) ExampleI-a-7 500 90

Example B

Phaedon Larvae Test

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with larvae of the mustard beetle (Phaedon cochleariae) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae has been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity:

TABLE B Plant-damaging insects Phaedon larvae test Concentration ofactive compound Kill rate Active compounds in ppm in % after 7^(d)Example I-a-7 500 100 Example I-c-1 500 100

Example C

Spodoptera frugiperda Test

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the armyworm (Spodoptera frugiperda)while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars has been killed.

In this test, for example, the following compound of the PreparationExamples shows good activity:

TABLE C Plant-damaging insects Spodoptera frugiperda test Concentrationof active compound Kill rate Active compounds in ppm in % after 7^(d)Example I-c-1 500 100

Example D

Tetranychus Test (OP-Resistant/dip Treatment)

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Bean plants (Phaseolus vulgaris) which are heavily infested by allstages of the greenhouse red spider mite (Tetranychus urticae) aredipped into a preparation of active compound of the desiredconcentration.

After the desired period of time, the effect in % is determined. 100%means that all spider mites have been killed; 0% means that none of thespider mites has been killed.

In this test, for example, the following compounds of the PreparationExamples show good activity:

TABLE D Plant-damaging mites Tetranychus test (OP-resistant/diptreatment) Concentration of active compound Kill rate Active compoundsin ppm in % after 7^(d) Example I-a-7 100 100 Example I-c-1 100 98

Example E

Critical Concentration Test/Soil Insects—Treatment of Transgenic Plants

Test Insect: Diabrotica balteata—Larvae in Soil

-   Solvent: 7 parts by weight of acetone-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

The preparation of active compound is poured onto the soil. Here, theconcentration of active compound in the preparation is virtuallyimmaterial, only the amount by weight of active compounds per volumeunit of soil, which is stated in ppm (mg/l), matters. The soil is filledinto 0.25 l pots, and these are allowed to stand at 20° C.

Immediately after the preparation, 5 pregerminated maize corns of thecultivar YIELD GUARD (trade mark of Monsanto Comp., USA) are placed intoeach pot. After 2 days, the appropriate test insects are placed into thetreated soil. After a further 7 days, the efficacy of the activecompound is determined by counting the maize plants that have emerged (1plant=20% activity).

Example F

Heliothis virescens Test—Treatment of Transgenic Plants

-   Solvent: 7 parts by weight of acetone-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent and thestated amount of emulsifier, and the concentrate is diluted with waterto the desired concentration.

Soybean shoots (Glycine max) of the cultivar Roundup Ready (trade markof Monsanto Comp. USA) are treated by being dipped into the preparationof active compound of the desired concentration and are populated withthe tobacco budworm Heliothis virescens while the leaves are stillmoist.

After the desired period of time, the kill of the insects is determined.

1. A compound represented by formulas (I-A) and/or (1-B)

in which (a) W represents hydrogen, halogen, C₁–C₆-alkyl, orC₁–C₆-alkoxy, X represents halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy,C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, or cyano, Y in the 4-positionrepresents hydrogen, C₁–C₆-alkoxy, halogen, cyano, or C₁–C₄-haloalkyl,and Z in the 3- or 5-position represents hydrogen or C₁–C₆-alkyl, or (b)W represents hydrogen, halogen, or C₁–C₆-alkyl, X represents halogen,C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, or cyano,Y in the 4-position represents a radical

in which V¹ represents hydrogen, halogen, C₁–C₁₂-alkyl, C₁–C₆-alkoxy,C₁–C₆-alkylthio, C₁–C₆-alkylsulphinyl, C₁–C₆-alkylsulphonyl,C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, nitro, or cyano or represents phenyl,phenoxy, phenoxy-C₁–C₄-alkyl, phenyl-C₁–C₄-alkoxy,phenylthio-C₁–C₄-alkyl, or phenyl-C₁–C₄-alkylthio, each of which isoptionally mono- or polysubstituted by halogen, C₁–C₆-alkyl,C₁–C₆-alkoxy, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, nitro, or cyano, and V²and V³ independently of one another represent hydrogen, halogen,C₁–C₆alkyl, C₁–C₆-alkoxy, C₁–C₄-haloalkyl, or C₁–C₄-haloalkoxy, or V¹and V² together represent C₃–C₄-alkanediyl that is optionallysubstituted by halogen and/or C₁–C₂-alkyl and that is optionallyinterrupted by one or two oxygen atoms, and Z represents hydrogen, or(c) W represents hydrogen, halogen, or C₁–C₆-alkyl, X representshalogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy,or cyano, Y in the 4-position represents hydrogen, C₁–C₆-alkyl, orhalogen, and Z in the 5-position represents a radical

 in which V¹ represents hydrogen, halogen, C₁–C₁₂-alkyl, C₁–C₆-alkoxy,C₁–C₆-alkylthio, C₁–C₆-alkylsulphinyl, C₁–C₆-alkylsulphonyl,C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, nitro, or cyano; or representsphenyl, phenoxy, phenoxy-C₁–C₄-alkyl, phenyl-C₁–C₄-alkoxy,phenylthio-C₁–C₄-alkyl, or phenyl-C₁–C₄-alkylthio, each of which isoptionally mono- or polysubstituted by halogen, C₁–C₆-alkyl,C₁–C₆-alkoxy, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, nitro, or cyano, and V²and V³ independently of one another represent hydrogen, halogen,C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₄-haloalkyl, or C₁–C₄-haloalkoxy, or V¹and V² together represent C₃–C₄-alkanediyl that is optionallysubstituted by halogen and/or C₁–C₂-alkyl and that is optionallyinterrupted by one or two oxygen atoms, or (d) W represents hydrogen,methyl, propyl, isopropyl or halogen, X represents halogen, C₁–C₆-alkyl,C₁–C₆-alkoxy, C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy, or cyano, Y in the4-position represents hydrogen, halogen, C₁–C₆-alkyl, C₁–C₄-haloalkyl,cyano, or C₁–C₄-haloalkoxy, and Z in the 3- or 5-position representshydrogen, halogen, or C₁–C₆-alkyl, and A represents hydrogen; representsoptionally halogen-substituted C₁–C₁₂-alkyl, C₃–C₈-alkenyl,C₁–C₁₀-alkoxy-C₁–C₈-alkyl, poly-C₁–C₈-alkoxy-C₁–C₈-alkyl, orC₁–C₁₀-alkylthio-C₁–C₆-alkyl; or represents optionally halogen-,C₁–C₆alkyl-, or C₁–C₆-alkoxy-substituted C₃–C₈-cycloalkyl in which oneor two ring members that are not directly adjacent are optionallyreplaced by oxygen and/or sulphur, B represents hydrogen, C₁–C₁₂-alkyl,or C₁–C₈-alkoxy-C₁–C₆-alkyl, or A, B, and the carbon atom to which theyare attached represent saturated C₃–C₁₀-cycloalkyl or unsaturatedC₅–C₁₀-cycloalkyl in which one ring member is optionally replaced byoxygen or sulphur and that are optionally mono- or disubstituted byC₁–C₈-alkyl, C₃–C₁₀-cycloalkyl, C₁–C₈-haloalkyl, C₁–C₈-alkoxy,C₁–C₈-alkylthio, halogen, or phenyl, D represents hydrogen; representsoptionally halogen-substituted C₁–C₁₂-alkyl, C₃–C₈-alkenyl,C₁–C₁₀-alkoxy-C₂–C₈-alkyl, poly-C₁–C₈-alkoxy-C₂–C₈-alkyl,C₁–C₁₀-alkylthio-C₂–C₈-alkyl, optionally halogen-, C₁–C₄-alkyl-,C₁–C₄-alkoxy-, or C₁–C₄-haloalkyl-substituted C₃–C₈-cycloalkyl in whichone ring member is optionally replaced by oxygen or sulphur, and Grepresents hydrogen (a) or represents one of the groups

 in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur, M represents oxygen or sulphur, R¹represents optionally halogen-substituted C₁–C₂₀-alkyl, C₂–C₂₀-alkenyl,C₁–C₈-alkoxy-C₁–C₈-alkyl, C₁–C₈-alkylthio-C₁–C₈-alkyl,poly-C₁–C₈-alkoxy-C₁–C₈-alkyl or optionally halogen-, C₁–C₆-alkyl-, orC₁–C₆-alkoxy-substituted C₃–C₈-cycloalkyl in which one or more ringmembers that are not directly adjacent are optionally replaced by oxygenand/or sulphur; represents optionally halogen-, cyano-, nitro-,C₁–C₆-alkyl-, C₁–C₆-alkoxy-, C₁–C₆-haloalkyl-, C₁–C₆-haloalkoxy-,C₁–C₆-alkylthio-, or C₁–C₆-alkylsulfonyl-substituted phenyl; representsoptionally halogen-, nitro-, cyano-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-,C₁–C₆-haloalkyl-, or C₁–C₆-haloalkoxy-substituted phenyl-C₁–C₆-alkyl;represents optionally halogen- or C₁–C₆-alkyl-substituted 5- or6-membered hetaryl; represents optionally halogen- orC₁–C₆-alkyl-substituted phenoxy-C₁–C₆-alkyl; or represents optionallyhalogen-, amino-, or C₁–C₆-alkyl-substituted 5- or 6-memberedhetaryloxy-C₁–C₆-alkyl, R² represents optionally halogen-substitutedC₁–C₂₀-alkyl, C₂–C₂₀-alkenyl, C₁–C₈-alkoxy-C₂–C₈-alkyl, orpoly-C₁–C₈-alkoxy-C₂–C₈-alkyl; represents optionally halogen-,C₁–C₆-alkyl-, or C₁–C₆-alkoxy-substituted C₃–C₈-cycloalkyl; orrepresents optionally halogen-, cyano-, nitro-, C₁–C₆-alkyl-,C₁–C₆-alkoxy-, C₁–C₆-haloalkyl-, or C₁–C₆-haloalkoxy-substituted phenylor benzyl, R³ represents optionally halogen-substituted C₁–C₈-alkyl; orrepresents optionally halogen-, C₁–C₆-alkyl-, C₁–C₆-alkoxy-,C₁–C₄-haloalkyl-, C₁–C₄-haloalkoxy-, cyano-, or nitro-substituted phenylor benzyl, R⁴ and R⁵ independently of one another represent optionallyhalogen-substituted C₁–C₈-alkyl, C₁–C₈-alkoxy, C₁–C₈-alkylamino,di(C₁–C₈-alkyl)amino, C₁–C₈-alkylthio, C₂–C₈-alkenylthio, orC₃–C₇-cycloalkylthio; or represent optionally halogen-, nitro-, cyano-,or C₁–C₄-alkoxy-, C₁–C₄-haloalkoxy-, C₁–C₄-alkylthio-,C₁–C₄-haloalkylthio-, C₁–C₄-alkyl-, or C₁–C₄-haloalkyl-substitutedphenyl, phenoxy, or phenylthio, and R⁶ and R⁷ independently of oneanother represent hydrogen; represent optionally halogen-substitutedC₁–C₈-alkyl, C₃–C₈-cycloalkyl, C₁–C₈-alkoxy, C–C₈-alkenyl, orC₁–C₈-alkoxy-C₁–C₈-alkyl; represent optionally halogen-,C₁–C₈-haloalkyl-, C₁–C₈-alkyl-, or C₁–C₈-alkoxy-substituted phenyl: orrepresent optionally halogen-, C₁–C₈-alkyl-, C₁–C₈-haloalkyl-, orC₁–C₈-alkoxy-substituted benzyl; or R⁶ and R⁷ together with the nitrogenatom to which they are attached represent optionallyC₁–C₄-alkyl-substituted C₄–C₇-cycloalkyl in which one carbon atom isoptionally replaced by oxygen or sulphur.
 2. A compound according toclaim 1 in which (a) W represents hydrogen, chlorine, bromine,C₁–C₄-alkyl, or C₁–C₄-alkoxy, X represents chlorine, bromine,C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy, or cyano,Y in the 4-position represents hydrogen, C₁–C₄-alkoxy, chlorine,bromine, cyano, or C₁–C₂-haloalkyl, and Z in the 3- or 5-positionrepresents hydrogen or C₁–C₄-alkyl, or (b) W represents hydrogen,chlorine, bromine, or C₁–C₄-alkyl, X represents chlorine, bromine,C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy, or cyano,Y in the 4-position represents a radical

 in which V¹ represents hydrogen, fluorine, chlorine, bromine,C₁–C₆-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy, nitro, orcyano; or represents phenyl that is optionally mono- or disubstituted byfluorine, chlorine, bromine, C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl,C₁–C₂-haloalkoxy, nitro, or cyano, and V² and V³ independently of oneanother represent hydrogen, fluorine, chlorine, bromine, C₁–C₄-alkyl,C₁–C₄-alkoxy, C₁–C₂-haloalkyl, or C₁–C₂-haloalkoxy, or V¹ and V²together represent —O—CH₂—O— or —O—CF₂—O—, and Z represents hydrogen, or(c) W represents hydrogen, chlorine, bromine, or C₁–C₄-alkyl, Xrepresents chlorine, C₁–C₄-alkyl, or C₁–C₂-haloalkyl, Y in the4-position represents hydrogen, C₁–C₄-alkyl, or chlorine, and Z in the5-position represents a radical

 in which V¹ represents hydrogen, fluorine, chlorine, bromine,C₁–C₆-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy, nitro, orcyano; or represents phenyl that is optionally mono- or disubstituted byfluorine, chlorine, bromine, C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl,C₁–C₂-haloalkoxy, nitro, or cyano, and V² and V³ independently of oneanother represent hydrogen, fluorine, chlorine, bromine, C₁–C₄-alkyl,C₁–C₄-alkoxy, C₁–C₂-haloalkyl, or C₁–C₂-haloalkoxy, or V¹ and V²together represent —O—CH₂—O— or —O—CF₂—O—, or (d) W represents hydrogen,methyl, chlorine, or bromine, X represents chlorine, bromine,C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy, or cyano,Y in the 4-position represents hydrogen, chlorine, bromine, C₁–C₄-alkyl,C₁–C₂-haloalkyl, cyano, or C₁–C₂-haloalkoxy, and Z in the 3- or5-position represents hydrogen, chlorine, bromine, or C₁–C₄-alkyl, and Arepresents hydrogen; represents C₁–C₁₀-alkyl orC₁–C₈-alkoxy-C₁–C₆-alkyl, each of which is optionally mono- totrisubstituted by fluorine or chlorine; represents C₃–C₇-cycloalkyl thatis optionally mono- or disubstituted by fluorine, chlorine, C₁–C₄-alkyl,or C₁–C₄-alkoxy and in which one ring member is optionally replaced byoxygen or sulphur, B represents hydrogen or C₁–C₆-alkyl, or A, B, andthe carbon atom to which they are attached represent saturated orunsaturated C₅–C₇-cycloalkyl in which one ring member is optionallyreplaced by oxygen or sulphur and that is optionally monosubstituted byC₁–C₆-alkyl, C₅–C₈-cycloalkyl, C₁–C₃-haloalkyl, or C₁–C₆-alkoxy, Drepresents hydrogen; represents C₁–C₁₀-alkyl, C₃–C₆-alkenyl,C₁–C₆-alkoxy-C₂–C₄-alkyl, or C₁–C₄-alkylthio-C₂–C₄-alkyl, each of whichis optionally mono- to trisubstituted by fluorine or chlorine:represents C₃–C₇-cycloalkyl that is optionally substituted by fluorine,chlorine, C₁–C₄-alkyl, C₁–C₄-alkoxy, or C₁–C₂-haloalkyl and in which onemethylene group is optionally replaced by oxygen or sulphur, and Grepresents hydrogen (a) or represents one of the groups

 in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur, M represents oxygen or sulphur, R¹represents C₁–C₁₆-alkyl, C₂–C₁₆-alkenyl, C₁–C₆-alkoxy-C₁–C₆-alkyl,C₁–C₄-alkylthio-C₁–C₄-alkyl, or poly-C₁–C₄-alkoxy-C₁–C₄-alkyl, each ofwhich is optionally mono- to trisubstituted by fluorine or chlorine; orrepresents C₃–C₇-cycloalkyl that is optionally mono- or disubstituted byfluorine, chlorine, C₁–C₄-alkyl, or C₁–C₄-alkoxy and in which one or tworing members that are not directly adjacent are optionally replaced byoxygen and/or sulphur; represents phenyl that is optionally mono- ordisubstituted by fluorine, chlorine, bromine, cyano, nitro, C₁–C₄-alkyl,C₁–C₄-alkoxy, C₁–C₃-haloalkyl, C₁–C₃-haloalkoxy, C₁–C₄-alkylthio, orC₁–C₄-alkylsulphonyl; represents phenyl-C₁–C₄-alkyl that is optionallymono- or disubstituted by fluorine, chlorine, bromine, C₁–C₄-alkyl,C₁–C₄-alkoxy, C₁–C₃-haloalkyl, or C₁–C₃-haloalkoxy; representspyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl, or thienyl, each ofwhich is optionally monosubstituted by fluorine, chlorine, bromine, orC₁–C₄-alkyl; or represents phenoxy-C₁–C₃-alkyl that is optionally mono-or disubstituted by fluorine, chlorine, bromine, or C₁–C₄-alkyl, R²represents C₁–C₁₆-alkyl, C₂–C₁₆-alkenyl, C₁–C₆-alkoxy-C₂–C₆-alkyl, orpoly-C₁–C₆-alkoxy-C₂–C₆-alkyl, each of which is optionally mono- totrisubstituted by fluorine; represents C₃–C₇-cycloalkyl that isoptionally mono- or disubstituted by fluorine, chlorine, C₁–C₄-alkyl, orC₁–C₄-alkoxy; or represents phenyl or benzyl, each of which isoptionally mono- or disubstituted by fluorine, chlorine, bromine, cyano,nitro, C₁–C₄-alkyl, C₁–C₃-alkoxy, C₁–C₃-haloalkyl, or C₁–C₃-haloalkoxy;R³ represents C₁–C₆-alkyl that is optionally mono- to trisubstituted byfluorine; or represents phenyl or benzyl, each of which is optionallymono- or disubstituted by fluorine, chlorine, bromine, C₁–C₄-alkyl,C₁–C₄-alkoxy, C₁–C₃-haloalkyl, C₁–C₃-haloalkoxy, cyano, or nitro, R⁴represents C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₆-alkylamino,di(C₁–C₆-alkyl)amino, C₁–C₆-alkylthio, C₃–C₄-alkenylthio, orC₃–C₆-cycloalkylthio; or represents phenyl, phenoxy, or phenylthio, eachof which is optionally mono- or disubstituted by fluorine, chlorine,bromine, nitro, cyano, C₁–C₃-alkoxy, C₁–C₃-haloalkoxy, C₁–C₃-alkylthio,C₁–C₃-haloalkylthio, C₁–C₃-alkyl, or C₁–C₃-haloalkyl, R⁵ representsC₁–C₄-alkoxy or C₁–C₄-alkylthio, R⁶ represents C₁–C₆-alkyl,C₃–C₆-cycloalkyl, C₁–C₆-alkoxy, C₃–C₆-alkenyl, orC₁–C₆-alkoxy-C₁–C₆-alkyl; represents phenyl that is optionally mono- ordisubstituted by fluorine, chlorine, bromine, C₁–C₃-haloalkyl,C₁–C₄-alkyl, or C₁–C₄-alkoxy; represents benzyl that is optionally mono-or disubstituted by fluorine, chlorine, bromine, C₁–C₄-alkyl,C₁–C₃-haloalkyl, or C₁–C₄-alkoxy, and R⁷ represents hydrogen,C₁–C₆-alkyl, or C₃–C₆-alkenyl, or R⁶ and R⁷ together with the nitrogenatom to which they are attached represent C₅–C₆-cycloalkyl that isoptionally mono- or disubstituted by methyl or ethyl and in which onemethylene group is optionally replaced by oxygen or sulphur.
 3. Acompound according to claim 1 in which (a) W represents hydrogen,chlorine, methyl, ethyl, or methoxy, X represents chlorine, bromine,methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy,trifluoroethoxy, or cyano, Y in the 4-position represents hydrogen,methoxy, chlorine, bromine, or trifluoromethyl, and Z in the 3- or5-position represents hydrogen or methyl, or (b) W represents hydrogen,chlorine, bromine, or methyl, X represents chlorine, bromine, methyl,ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy, or cyano, Y inthe 4-position represents the radical

 in which V¹ represents hydrogen, fluorine, chlorine, bromine, methyl,ethyl, n-propyl, isopropyl, tert-butyl, methoxy ethoxy, n-propoxy,isopropoxy, trifluoromethyl, or trifluoromethoxy, and V² representshydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl,methoxy, ethoxy, or trifluoromethyl, and Z represents hydrogen, or (c) Wrepresents hydrogen, chlorine, or methyl, X represents chlorine, methyl,or trifluoromethyl, Y in the 4-position represents hydrogen or methyl,and Z in the 5-position represents the radical

 in which V¹ represents hydrogen, fluorine, chlorine, bromine, methyl,ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, n-propoxy,isopropoxy, trifluoromethyl, or trifluoramethoxy, and V² representshydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, isopropyl,methoxy, ethoxy, or trifluoromethyl, or (d) W represents hydrogen,methyl, chlorine, or bromine, X represents chlorine, bromine, methyl,methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, or cyano, Yin the 4-position represents hydrogen, chlorine, bromine, methyl,trifluoromethyl, or trifluoromethoxy, and Z in the 3- or 5-positionrepresents hydrogen, chlorine, bromine, or methyl, and A representshydrogen, C₁–C₄-alkyl, or C₁–C₄-alkoxy-C₁–C₂-alkyl; representsC₃–C₆-cycloalkyl that is optionally monosubstituted by fluorine, methyl,ethyl, or methoxy and in which optionally one ring member is replaced byoxygen or sulphur, B represents hydrogen, methyl, or ethyl, or A, B, andthe carbon atom to which they are attached represent saturatedC₅–C₆-cycloalkyl in which one ring member is optionally replaced byoxygen and that is optionally monosubstitiuted by methyl, ethyl, propyl,isopropyl, butyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy, orisobutoxy, D represents hydrogen; represents C₁–C₈-alkyl, C₃–C₄-alkenyl,C₁–C₆-alkoxy-C₂–C₄-alkyl, C₁–C₄-alkylthio-C₂–C₄-alkyl, orC₃–C₆-cycloalkyl, each of which is optionally mono- to trisubstituted byfluorine, and G represents hydrogen (a) or represents one of the groups

 in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur, M represents oxygen or sulphur, R¹represents C₁–C₁₀-alkyl, C₂–C₁₀-alkenyl, C₁–C₂-alkoxy-C₁–C₂-alkyl, orC₁–C₂-alkylthio-C₁–C₂-alkyl, each of which is optionally mono- totrisubstituted by fluorine or chlorine; or represents C₃–C₆-cycloalkylthat is optionally mono- or disubstituted by fluorine, chlorine, methyl,ethyl, propyl, isopropyl, butyl, i-butyl, tert-butyl, methoxy, ethoxy,n-propoxy, or isopropoxy and in which one ring member is optionallyreplaced by oxygen; represents phenyl that is optionally mono- ordisubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl,ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy,trifluoromethyl, or trifluoromethoxy; represents benzyl that isoptionally mono- or disubstituted by fluorine, chlorine, bromine,methyl, methoxy, trifluoromethyl, or trifluoromethoxy; or representsfuranyl, thienyl, pyridyl, pyrimidyl, thiazolyl, or pyrazolyl, each ofwhich is optionally substituted by fluorine, chlorine, bromine, methyl,or ethyl; R² represents C₁–C₁₀-alkyl, C₂–C₁₀-alkenyl, orC₁–C₄-alkoxy-C₂–C₃-alkyl, each of which is optionally mono- totrisubstituted by fluorine; represents C₃–C₆-cycloalkyl that isoptionally monosubstituted by fluorine, chlorine, methyl, ethyl, ormethoxy; or represents phenyl or benzyl, each of which is optionallymonosubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl,n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl, ortrifluoromethoxy, R³ represents methyl, ethyl, or n-propyl; orrepresents phenyl that is optionally monosubstituted by fluorine,chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano, or nitro, R⁴ represents C₁–C₄-alkyl,C₁–C₄-alkoxy, C₁–C₄-alkylamino, di(C₁–C₄-alkyl)amino, orC₁–C₄-alkylthio; or represents phenoxy or phenylthio, each of which isoptionally monosubstituted by fluorine, chlorine, bromine, nitro, cyano,C₁–C₂-alkoxy, C₁–C₂-fluoroalkoxy, C₁–C₂-alkylthio,C₁–C₂-fluoroalkylthio, or C₁–C₃-alkyl, R⁵ represents methoxy, ethoxy,methylthio, or ethylthio, R⁶ represents C₁–C₄-alkyl, C₃–C₆-cycloalkyl,C₁–C₄-alkoxy, C₃–C₄-alkenyl, or C₁–C₄-alkoxy-C₁–C₄-alkyl; representsphenyl that is optionally mono- or disubstituted by fluorine, chlorine,bromine, trifluoromethyl, methyl, or methoxy; or represents benzyl thatis optionally monosubstituted by fluorine, chlorine, bromine, methyl,trifluoromethyl, or methoxy, and R⁷ represents hydrogen, methyl, ethyl,propyl, isopropyl, butyl, or allyl, or R⁶ and R⁷ together with thenitrogen atom to which they are attached represent C₅–C₆-cycloalkyl thatis optionally mono- or disubstituted by methyl and in which onemethylene group is optionally replaced by oxygen.
 4. A compoundaccording to claim 1 in which (a) W represents hydrogen, methyl, ethyl,or chlorine, X represents methyl or chlorine, Y in the 4-positionrepresents methoxy, chlorine, bromine, or trifluoromethyl, Z in the5-position represents hydrogen or methyl, A represents methyl, Brepresents methyl, D represents methyl or hydrogen, and G representshydrogen, or (b) W represents hydrogen, X represents methyl or chlorine,Y represents hydrogen, Z in the 5-position represents

A represents methyl, B represents methyl, or A and B together represent(CH₂)₃—, D represents methyl, and G represents hydrogen (a) orrepresents one of the groups

in which R¹ represents C₁–C₆-alkyl, and R² represents C₁–C₆-alkyl, or(c) W represents hydrogen or methyl, X represents methyl or bromine, Yin the 4-position represents methyl, Z in the 3- or 5-positionrepresents methyl or hydrogen, A moreover represents methyl, B moreoverrepresents methyl, or A and B together represent —(CH₂)₄, D representsmethyl, and G represents hydrogen (a) or represents one of the groups

 in which R¹ represents C₁–C₆-alkyl, and R² represents C₁–C₆-alkyl.
 5. Aprocess for preparing compounds according to claim 1 comprising (A) forcompounds of formula (I-a)

 in which A, B, D, W, X, Y, and Z are as defined in claim 1,intramolecularly condensing an N-acylhydroxyamino acid ester of formula(II)

in which A, B, D, W, X, Y, and Z are as defined in claim 1, and R⁸represents alkyl, in the presence of a diluent and in the presence of abase; (B) for compounds of the formula (I-b)

 in which A, B, D, R¹, W, X, Y, and Z are as defined in claim 1,reacting a compound of formula (I-a), in which A, B, D, W, X, Y and Zare as defined in claim 1, (α) with an acid halide of formula (III)

 in which R¹ is as defined in claim 1, and Hal represents halogen, or(β) with a carboxylic anhydride of formula (IV)R¹—CO—O—CO—R¹  (IV)  in which R¹ is as defined in claim 1, optionally inthe presence of a diluent and optionally in the presence of an acidbinder; (C) for compounds of formula (I-c)

 in which A, B, D, R², M, W, X, Y, and Z are as defined in claim 1, andL represents oxygen, reacting a compound of formula (I-a), in which A,B, D, W, X, Y, and Z are as defined in claim 1, with a chloroformicester or chloroformic thioester of formula (V)R²-M-CO—Cl  (V) in which R² and M are as defined in claim 1, optionallyin the presence of a diluent and optionally in the presence of an acidbinder; (D) for compounds of formula (I-c)

 in which A, B, D, R², M, W, X, Y, and Z are as defined in claim 1, andL represents sulphur, reacting a compound of formula (I-a), in which A,B, D, W, X, Y, and Z are as defined in claim 1, with achloromonothioformic ester or chlorodithioformic ester of formula (VI)

in which M and R² am as defined in claim 1, optionally in the presenceof a diluent and optionally in the presence of an acid binder; (E) forcompounds of formula (I-d)

 in which A, B, D, R³, W, X, Y, and Z are as defined in claim 1,reacting a compound of formula (I-a), in which A, B, D, W, X, Y, and Zare as defined in claim 1, with a sulphonyl chloride of formula (VII)R³—SO₂—Cl  (VII) in which R³ is as defined in claim 1, optionally in thepresence of a diluent and optionally in the presence of an acid binder,(F) for compounds of the formula (I-e)

 in which A, B, D, L, R⁴, R⁵, W, X, Y, and Z are as defined in claim 1,reacting a compound of formula (I-a) in which A, B, D, W, X, Y, and Zare as defined in claim 1, with a phosphorus compound of formula (VIII)

in which L, R⁴, and R⁵ are as defined in claim 1, and Hal representshalogen, optionally in the presence of a diluent and optionally in thepresence of an acid binder, (G) for compounds of formula (I-f)

 in which A, B, D, E, W, X, Y and Z are as defined in claim 1, reactinga compound of formula (I-a), in which A, B, D, W, X, Y, and Z are asdefined in claim 1, with a metal compound of formula (IX)Me(OR10)_(t)  (IX) in which Me represents a mono- or divalent metal, trepresents the number 1 or 2, and R¹⁰ represents hydrogen or alkyl, oran amine of formula (X)

in which R¹¹ and R¹² independently of one another represent hydrogen oralkyl, optionally in the presence of a diluent, (H) for compounds of theformula (I-g)

 in which A, B, D, L, R⁶, R⁷, W, X, Y and Z are as defined in claim 1,reacting a compound of formula (I-a), in which A, B, D, W, X, V, and Zare as defined in claim 1, (α) with an isocyanate or isothiocyanate offormula (XI)R⁶—N=C=L  (XI)  in which R⁶ and L are as defined in claim 1, optionallyin the presence of a diluent and optionally in the presence of acatalyst, or (β) with a carbamoyl chloride or thiocarbamoyl chloride offormula (XII)

 in which L, R⁶, and R⁷ are as defined in claim 1, optionally in thepresence of a diluent and optionally in the presence of an acid binder.6. A compound of formula (II)

in which (a) W represents hydrogen, halogen, alkyl, or alkoxy, Xrepresents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, Y inthe 4-position represents hydrogen, alkoxy, halogen, cyano, orhaloalkyl, and Z in the 3- or 5-position represents hydrogen or alkyl,or (b) W represents hydrogen, halogen, or alkyl, X represents halogen,alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, Y in the 4-positionrepresents optionally substituted aryl or hetaryl, and Z representshydrogen, or (c) W represents hydrogen, halogen, or alkyl, X representshalogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, Y in the4-position represents hydrogen, alkyl, or halogen, and Z in the5-position represents optionally substituted aryl or hetaryl, or (d) Wrepresents hydrogen, methyl, propyl, isopropyl, or halogen, X representshalogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, Y in the4-position represents hydrogen, halogen, alkyl, haloalkyl, cyano, orhaloalkoxy, and Z in the 3- or 5-position moreover represents hydrogen,halogen, or alkyl, and A represents hydrogen; represents optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, oralkylthioalkyl; or represents saturated or unsaturated optionallysubstituted cycloalkyl in which one or more ring atoms are optionallyreplaced by a heteroatam, B represents hydrogen, alkyl, or alkoxyalkyl,or A and B together with the carbon atom to which they are attachedrepresent a saturated or unsaturated unsubstituted or substituted cyclethat optionally contains one or more heteroatoms, D represents hydrogenor an optionally substituted radical selected from the group consistingof alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, andsaturated or unsaturated cycloalkyl in which one or more ring membersare optionally replaced by heteroatoms, and R⁸ represents alkyl.
 7. Apesticide, microbicide, or herbicide composition comprising one or morecompounds according to claim 1 and one or more extenders and/orsurfactants.
 8. A method for controlling animal pests comprisingallowing an effective amount of one or more compounds according to claim1 to act on animal pests and/or their habitat.
 9. A method forcontrolling unwanted vegetation comprising allowing an effective amountof one or more compounds according to claim 1 to act on unwantedvegetation and/or their habitat.
 10. A method for controlling fungicomprising allowing an effective amount of one or more compoundsaccording to claim 1 to act on fungi and/or their habitat.
 11. A processfor preparing a pesticide, microbicide, or herbicide compositioncomprising mixing one or more compounds according to claim 1 with one ormore extenders and/or surfactants.